Category: Tetrahydropyrans

65412-03-5, 4-(2-Aminoethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,65412-03-5

5- (4-bromomethyl-2-methoxyphenoxy) pyrazine-2-carboxamide (starting from 5- (4-bromomethyl-2-methoxybenzeneOxy) pyrazine-2-carboxamide was added in the same manner as in Groups 1 to 5, respectively, and the amount of the added amount2), 5.3 g (41 mmol) of 2- (tetrahydropyran-4-yl) ethylamine, 187 ml of dichloromethane was added to a 250 ml three-necked flask, The reaction system was heated to reflux (40 C) and reacted under reflux for 4 hours. After the reaction time, the reaction was stopped and the pressure wasConcentrated by heating and concentrated to complete a solid which was stirred with 100 ml of water for 1 hour, filtered and dried to about 11G of a white solid which was added to 300 ml of ethyl acetate, washed with 100 ml of 2M aqueous sodium hydroxide solution, and the organic phaseWashed with 100 ml of X2 and the organic phase dried to give 10 g of a white solid (yield: 75.7%, purity: 98.5%). Table 2 showsEffect of the amount of 2- (tetrahydropyran-4-yl) ethylamine on the yield and purity of the product.(3) times purified Fupu Lan10 g of a white solid was placed in a 100 ml three-necked flask,Add 60 ml of isopropyl alcohol, start heating,At 65 under the basic full solution, continue to heat,And adding 0.7 g of activated carbon,Heating at 70-75 C for 30 minutes, followed by hot filtration,The filtrate gradually cooled to room temperature,And continue to stir in the ice bath for 1.5 hours, filter, dry,9.0 g of a white crystalline solid (yield: 68%, purity: 99.8%),The filtered mother liquor was concentrated and 0.3 g of solid (94.3% purity) was recovered.

65412-03-5 4-(2-Aminoethyl)tetrahydro-2H-pyran 2773198, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Shandong Chuancheng Pharmaceutical Co., Ltd.; Liu, Huaizhen; Chen, Naitao; Guo, Ming; Ma, Juliang; (10 pag.)CN106117190; (2016); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.,4295-99-2

To a solution of tetrahydro-2H-pyran-4-carbonitrile (2 g, 18.00 mmol) in tetrahydrofuran (10 mL) at 0 – 5 C was added slowly LHMDS (21.59 mL, 21.59 mmol). The mixture was stirred for 1.5 hrs at 0 C. Iodomethane (3.37 mL, 54.0 mmol) was added slowly and stirring was continued for 30 min at ~0 C and then for ~2 hrs at room temperature. The mixture was cooled to 0 C and carefully diluted with IN aqueous hydrochloride solution (30 mL) and EtOAc (5 mL) and concentrated under reduced pressure. The residue was taken up in diethylether and the separated organic layer was washed with brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4-methyltetrahydro-2H-pyran-4-carbonitrile (1.8 g) as an orange oil, which was directly used in the next reaction without further purification. LCMS (m/z): 126.1 [M+H]+; Rt = 0.44 min.

The synthetic route of 4295-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; BARSANTI, Paul A.; HU, Cheng; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WO2011/26904; (2011); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of Mg (1.37 g, 56.5 mmol) and I2(10 mg) in THF (2 mL) was added a solution of 4-chlorotetrahydro-2H-pyran (2.72 g, 22.6 mmol) in THF (8 mL) at 60C drop wise. The mixture was stirred at 60C for 2 h. The mixture was diluted with THF (10 mL) and used directly. The Grignard reagent was added to a solution of G-6 (0.55 g, 1.28 mmol) in THF (5 mL) at 0C. The mixture was stirred at 0C for 1 h and treated with NH4C1 (10 mL, sat. aq.). The mixture was extracted with EtOAc (3 x 20 mL). The organic layer was separated, concentrated in vacuum, purified by silica gel column (PE/EtOAc=20/l to 5/1) to give a crude product, which was re-crystallized from CH3CN (10 mL) to give Compound 9 (180 mg, 27%) as a solid.1H NMR (400 MHz, CDC13) delta 4.05-3.97 (m, 2H), 3.41-3.25 (m, 3H), 2.10-1.91 (m, 3H), 1.88- 1.57 (m, 7H), 1.55-1.33 (m, 11H), 1.33-0.96 (m, 12H), 0.96-0.86 (m, 4H), 0.85 (s, 3H), 0.72- 0.63 (m, 4H).HPLC Rt = 4.73 min in 8.0 min chromatography, 50-100 AB.MS ESI calcd. for C30H48F3O2[M+H-H20]+497, found 497., 1768-64-5

As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

Reference£º
Patent; SAGE THERAPEUTICS, INC.; SALITURO, Francesco G.; ROBICHAUD, Albert J.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd L.; GRIFFIN, Andrew; LA, Daniel; (387 pag.)WO2018/75699; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

General procedure: The N-hydroxy compounds were prepared by the following procedure. 4-substituted anhydride (1 mol) and hydroxylamine hydrochloride (1.14 mol) were suspended in isopropanol (150 mL). A solution of 46% sodium hydroxide solution (3 mol) was added to the mixture was and vigorously stirred for 4 h at 60-65C. The mixture was then acidified to pH 2 by 2 N HCl and extracted with dichloromethane. The dichloromethane layer was evaporated under vacuum the solid thus formed was filtered and recrystallized using methanol., 185815-59-2

The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ponnusamy, Kannan; Davis Presley; Nagapillai, Prakash; Deivanayagam, Eswaramoorthy; Indian Journal of Heterocyclic Chemistry; vol. 28; 2; (2018); p. 275 – 278;,
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Tetrahydropyran – an overview | ScienceDirect Topics

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53911-68-5, The solution of 3-(4-chlorophenyl)glutaric anhydride (449 mg) and anthranilamide (272 mg) in toluene (8 ml) was heated to reflux for 4 h. After removal of the solvent the residue was dried in vacuo. The off- white solid was dissolved in 2M sodium hydroxide (3 ml) and stirred under reflux for 2 h. After cooling to room temperature acetic acid (0.5 ml) was added with stirring. The precipitate formed was isolated by suction filtration, washed, and dried in vacuo to give 3-(4-chlorophenyl)-4-(4-hydroxy-2-quinazolinyl)butanoic acid (0.57 g) as colourless solid.1H-NMR (500 MHz, DMSO-d6)): delta (ppm)=2.62 (dd, J=16.0, 9.3 Hz, 1H), 2.74 (dd, J=16.0, 5.6 Hz, 1H), 2.86 (dd, J=14.4, 7.7 Hz, 1H), 2.93 (dd, J=14.4, 7.8 Hz, 1H), 3.74 (m, 1H), 7.32 (m, 4H), 7.44 (dt, J=8.0, 1.1 Hz, 1H), 7.59 (d, J=8.0, 1H), 7.76 (dt, J=7.7, 1.6 Hz, 1H), 8.04 (dd, J=7.9, 1.2 Hz, 1H), 12.10 (s, br, 1H), 12.20 (s, br, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=38.82 (CH), 39.37 (CH2), 40.75 (CH), 120.70 (C), 125.56 (CH), 125.98 (CH), 126.75 (CH), 128.07 (CH), 129.33 (CH), 130.90 (C), 134.19 (C), 142.22 (C), 148.59 (C), 155.17 (C), 161.59 (CO), 172.55 (CO).

The synthetic route of 53911-68-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

1408168-76-2, Potassium trifluoro(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)borate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A schlenk flask was charged with the compound obtained in example 1 (0.56 g, 1.3 mmol), bis(di-fe/f-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(ll) (94 mg, 0.13 mmol), potassium trifluoro(2-((tetrahydro-2/-/-pyran-2-yl)oxy)ethyl)borate (0.34 g, 1.6 mmol), and CS2CO3 (1.7 g, 5.3 mmol) and it was evacuated and backfilled with argon. Tolueneil-hO (4:1 , 10 mL) was added and the reaction mixture was heated at 100 C overnight. H2O was added and the product was extracted with EtOAc. The combined organic layers were dried over Na2S04, filtered and concentrated to dryness to give the title compound (0.62 g, Yield: 99%)., 1408168-76-2

1408168-76-2 Potassium trifluoro(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)borate 74787645, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ESTEVE PHARMACEUTICALS, S.A.; FERNANDEZ-DONIS, Ariadna; DIAZ-FERNANDEZ, Jose, Luis; ALMANSA-ROSALES, Carmen; LORENTE-CRIVILLE, Adriana; (0 pag.)WO2020/89400; (2020); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.

I: Toluene-4-sulfonic acid tetrahydropyran-4-ylmethyl ester Intermediate p-Toluenesulfonyl chloride (29.8 g, 157 mmol) was added portionwise to a mixture of tetrahydro-2H-pyran-4-yl-methanol (20.0 g, 172 mmol) and pyridine (25.2 ml, 313 mmol) in dichloromethane (200 ml). The mixture was stirred at room temperature for 17 h, then quenched with aqueous hydrochloric acid (2 M; 100 ml). The layers were separated and the aqueous layer extracted 2 with dichloromethane (2*100 ml). The organic layers were combined and concentrated in vacuo. Recrystallisation from dichloromethane:n-heptane (5:1) afforded toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester. The mother liquors were further purified by silica gel column chromatography eluding with 50% dichloromethane in n-heptane to yield a further quantity of toluene-4-sulfonic acid tetrahydropyran-4-ylmethyl ester (total yield 41.6 g, 154 mmol).

14774-37-9, The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; N.V. Organon; US2008/207598; (2008); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

5631-96-9, 2-(2-Chloroethoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5631-96-9, Example 19 (+-)-3-{1-[2-(Tetrahydro-2H-pyran-2-yloxy)ethyl]-trans-3,4-dimethylpiperidinyl}phenol To a solution of (+-)-3-(trans-3,4-dimethylpiperidinyl)phenol (60 mg, 0.29 mmol) in N,N-dimethylformamide (2.5 mL) at room temperature was added sodium hydrogencarbonate (27 mg, 0.32 mmol), sodium iodide (48 mg, 0.32 mmol) and 2-chloroethyl tetrahydro-2H-pyran-2-yl ether (52 mg, 0.32 mmol) in N,N-dimethylformamide (2.0 mL). The mixture was heated at 120 C. for 1.5 hours, cooled and then water (30 mL) and ethyl acetate (10 mL) were added. The two layers were separated and the aqueous layer was extracted with ethyl acetate (2*10 mL) and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude oil. This was purified by preparative HPLC on a Dynamax column, 42*250 mm; flow 8.0 mL min-1; employing U.V. detection at 275 nm; eluant gradient of acetonitrile:0.05 M aqueous ammonium acetate solution (90:10 to 10:90) to afford the title compound as its acetate salt. 1H-NMR (selected data from the acetate salt): 0.81 (d, 3H), 1.30 (s, 3H), 1.40-1.92 (m, 7H), 2.01-2.10 (m, 1H), 2.35 (m, 1H), 2.50-2.82 (m, 5H), 2.98 (m, 1H), 3.42-3.62 (m, 2H), 3.82-3.95 (m, 2H), 4.60 (m, 1H), 6.64 (d, 1H), 6.70-6.83 (m, 2H), 7.15 (t, 1H). MS (APCI+): m/z [MH+] 334.4; C20H31NO3+H requires 334.2.

As the paragraph descriping shows that 5631-96-9 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc.; US6518282; (2003); B1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1194-16-7, A) 4-(methoxymethylene)-2,2-dimethyltetrahydro-2H-pyran Thereto was added (methoxymethyl)triphenylphosphonium chloride (17.0 g), and the mixture was dried under reduced pressure at 100C for 1 hr. Under a nitrogen atmosphere, dehydrated THF (80 mL) was added, and potassium tert-butoxide (5.40 g) was further added at -30C. After 40 min, to the reaction mixture was added dropwise a solution of 2,2-dimethyltetrahydropyran-4-one (5.20 g) in dehydrated THF (5.0 mL) over 15 min, and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, and dried. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give an isomer mixture (E:Z = 1:1, 4.00 g) of the title compound as a colorless transparent oil. 1H NMR(400 MHz, CDCl3) delta 1.18 (6H, s), 1.20 (6H, s), 1.92 (2H, d, J = 1.2 Hz), 1.98-2.02 (2H, m), 2.17 (2H, d, J = 0.8 Hz), 2.23-2.26 (2H, m), 3.54 (3H, s), 3.56 (3H, s), 3.64-3.70 (4H, m), 5.77-5.78 (1H, m), 5.92-5.93 (1H, m).

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; MIWATASHI, Seiji; SUZUKI, Hideo; OKAWA, Tomohiro; MIYAMOTO, Yasufumi; YAMASAKI, Takeshi; HITOMI, Yuko; HIRATA, Yasuhiro; EP2816032; (2014); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0217] A solution of (tetrahydro-pyran-4-yl)-methanol (1.0 g, 8.61 mmol, prepared according to WO 99/00385) in methylene chloride (30 mL) at 25 C. was treated with 4-(dimethylamino)pyridine (1.17 g, 9.47 mmol) and p-toluenesulfonyl chloride (1.64 g, 8.61 mmol) and then was allowed to stir at 25 C. overnight. The reaction was then transferred to a separatory funnel and washed with a 1N aqueous hydrochloric acid solution (10 mL), a saturated aqueous sodium bicarbonate solution (10 mL), and a saturated aqueous sodium chloride solution (10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 75/25 hexanes/ethyl acetate) afforded toluene-4-sulfonic acid tetrahydro-pyran-4-yl methyl ester (1.77 g, 76%) as a colorless oil. [0218] A solution of toluene-4-sulfonic acid tetrahydro-pyran-4-yl methyl ester (1.77 g, 6.55 mmol) and sodium iodide (2.85 g, 18.99 mmol) in acetone (26 mL) was heated to 60 C. for 16 h. The resulting suspension was then cooled to 10 C. and filtered. The salts were rinsed with cold acetone (5 mL), and the filtrate and washings were concentrated in vacuo to a thick slurry. This slurry was treated with methylene chloride (10 mL). The resulting precipitate was removed by filtration and was washed with methylene chloride (10 mL). The filtrate and washings were then dried over magnesium sulfate, filtered through a pad of silica gel, and then concentrated in vacuo to afford 4-iodomethyl-tetrahydro-pyran as a light yellow oil. [0219] A solution of diisopropylamine (0.33 mL, 2.38 mmol) in tetrahydrofuran (6 mL) cooled to -78 C. under an argon atmosphere was treated with a 2.5M solution of n-butyllithium in hexanes (0.95 mL, 2.38 mmol). The reaction mixture was stirred at -78 C. for 15 min, after which time, a solution of (3-chloro-4-methylsulfanyl-phenyl)-acetic acid methyl ester (prepared as in Example 4, 500 mg, 2.17 mmol) in tetrahydrofuran (1 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (0.5 mL) was slowly added via a cannula. The greenish yellow solution was allowed to stir at -78 C. for 1 h, after which time, a solution of 4-iodomethyl-tetrahydro-pyran (588 mg, 2.60 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (0.5 mL) was added via a cannula. The reaction mixture was then allowed to warm to 25 C., where it was stirred for 16 h. The reaction mixture was then quenched by the addition of a saturated aqueous ammonium chloride solution (30 mL). This solution was extracted with ethyl acetate (3¡Á20 mL). The combined organic layers were washed with a 10% aqueous sulfuric acid solution (2¡Á50 mL) and a saturated aqueous sodium bicarbonate solution (2¡Á50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 75/25 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methylsulfanyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (431 mg, 61%) as a yellow oil: EI-HRMS m/e calcd for C16H21ClO3S (M+) 328.0900, found 328.0898. [0220] A solution of 2-(3-chloro-4-methylsulfanyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (200 mg, 0.61 mmol) in formic acid (0.23 mL) and tetrahydrofuran (0.5 mL) cooled to 0 C. was treated with a 30% aqueous hydrogen peroxide solution (0.35 mL, 3.04 mmol). The reaction was slowly warmed to 25 C. where it was stirred for 16 h. The reaction mixture was then cooled to 0 C., quenched with a saturated aqueous sodium sulfite solution, and then extracted with ethyl acetate (3¡Á20 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 60/40 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (190 mg, 87%) as a colorless oil: (ES)+-HRMS m/e calcd for C16H21ClO5S (M+Na)+ 383.0690, found 383.0692. [0221] A, 14774-37-9

14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Corbett, Wendy Lea; Grimsby, Joseph Samuel; Haynes, Nancy-Ellen; Kester, Robert Francis; Mahaney, Paige Erin; Racha, Jagdish Kumar; Sarabu, Ramakanth; Wang, Ka; US2003/225283; (2003); A1;,
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