Category: Tetrahydropyrans

10521-08-1, 2H-Pyran-2,4,6(3H,5H)-trione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

acetonedicarboxylic acid anhydride (31.4 kg) was added to methanol (100 L) cooled to 5 C. upon vigorous stirring. The resulting solution was kept at ambient temperature for 45 min to ensure that formation of acetone dicarboxylic acid monomethyl ester was complete.

10521-08-1, As the paragraph descriping shows that 10521-08-1 is playing an increasingly important role.

Reference£º
Patent; Cody Laboratories, Inc.; US7855296; (2010); B1;,
Tetrahydropyran – Wikipedia
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

General procedure: To the above THP ether solution(1 mmol)in methanol (10 mL),5 mol % bismuth trichloridewas added. The reaction mixture was stirred forappropriate time as provided in Table 1 at roomtemperature. The reaction was monitored by TLC.After completion of the reaction water was added tothe reaction mixture and the product was extractedwith ethyl acetate (3×25 mL). Later the combinedorganic layer was washed with brine, dried overanhydrous sodium sulphate and concentrated invacuum to give a crude mass, which was purifedover silica gel column to afford parent alcohol inquantitative yield., 5631-96-9

5631-96-9 2-(2-Chloroethoxy)tetrahydro-2H-pyran 254951, aTetrahydropyrans compound, is more and more widely used in various fields.

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Article; Vijaya Durga; Balamurali Krishna; Baby Ramana; Santha Kumari; Vijay; Hari Babu; Oriental Journal of Chemistry; vol. 33; 2; (2017); p. 1030 – 1034;,
Tetrahydropyran – Wikipedia
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

A mixture of 2,2-dimethyltetrahydropyran-4-one 1 (1.3 g, 0.01 mol)[8], furfural (1.0 g, 0.01 mol), ethyl cyanoacetic acid (1.1 g,0.01 mol), and ammonium acetate (6.2 g, 0.08 mol) in 30 mL of absolute ethanol was boiled with stirring for 6 h. After cooling, the crystals were filtered off, washed with water, diethyl ether, dried and recrystallized from ethanol. Yield 1.3 g (49 %), mp 289-290 C. IR spectrum, nu, cm-1: 3300, 3150, 3050 (N-H, C-H), 2240 (C?N), 1650 (C=O). 1H NMR spectrum, delta, ppm: 1.29 s (6H, 2CH3), 2.54 br. s(2H, CH2), 4.55 br. s (2H, OCH2), 6.68 d. d (1H, H4furan,J = 3.6, 1.7 Hz), 7.24 br. d (1H, H3furan, J= 3.6 Hz), 7.80 d.d (1H, H5furan, J = 1.7, 0.6 Hz), 12.46 br. s (1H, NH). 13C NMR spectrum, delta, ppm: 25.8, 37.3, 59.5, 68.8, 103.6, 108.0, 111.8, 115.6, 115.8, 143.7, 144.8, 146.1, 146.4, 159.9. Found, % C 66.59; H 5.31; N 10.32. C15H14N2O3. Calculated, %: C 66.66; H 5.22; N 10.36., 1194-16-7

As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Article; Dabaeva; Baghdasaryan; Paronikyan; Tamazyan; Ayvazyan; Dashyan, Sh. Sh.; Russian Journal of General Chemistry; vol. 89; 12; (2019); p. 2364 – 2368; Zh. Obshch. Khim.; vol. 89; 12; (2019); p. 1842 – 1847,6;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

693287-79-5, tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

693287-79-5, To stirred solution of tert-butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate (1.8 g, 8.33 mmol) in 1,4 dioxane (15 mL), HCl.dioxane (4 M, 10 mL) was added and stirred at room temperature for 1 h. Progress of the reaction was monitored by TLC. Upon completion the reaction mixture was evaporated under reduced pressure to obtain a residue which was triturated with diethyl ether and pentane, filtered and dried under reduced pressure to afford the title compound

The synthetic route of 693287-79-5 has been constantly updated, and we look forward to future research findings.

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Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; (178 pag.)WO2016/44666; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,29943-42-8

Step 1 Methylmagnesium bromide (3.66 mL, 10.99 mmol) was added dropwise via syringe to a solution of dihydro-2H-pyran-4(3H)-one (1 g, 9.99 mmol) in Diethyl ether (50 mL) at 0 C. and stirred at this temp for 1 hr before warming up to RT. The reaction was quenched with sat. ammonium chloride and extracted with ether. The organic layer was washed with brine, collected, dried over MgSO4, filtered and evaporated to give the crude product 4-methyltetrahydro-2H-pyran-4-ol (1 g, 86% yield) as an oil. 1H NMR (400 MHz, CHLOROFORM-d) delta 3.82-3.73 (m, 2H), 3.73-3.66 (m, 2H), 1.74-1.64 (m, 3H), 1.54 (ddt, J=13.7, 4.6, 2.1 Hz, 2H), 1.41 (br. s, 1H), 1.28 (s, 3H).

29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
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.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

A flask was charged with 4-hydroxytetrahydropyran (3.00 g, 29.4 mmol), Methanesulfonyl chloride (2.39mL, 30.9 mmol), triethylamine (8.20 mL, 58.8 mmol), and CH2Cl2. The resulting mixture was stirred overnight at room temperature. The reaction mixture was then washed with saturated aqueous NaHCO3 (100 mL) and water (100 mL), dried over Na2SO4, filtered and concentrated under reducedpressure. The crude product thus obtained was used without further purification.

2081-44-9, 2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
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.

Example 43 (Synthesis of 4-aminomethyltetrahydropyran) In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 200 ml were charged 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 50.0 g of 22% by weight ammonia-methanol solution and 2.0 g (17.0 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D), and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61MPa) at 45 to 55C for 17 hours under stirring. After completion of the reaction, insoluble materials were filtered, and the filtrated material was washed with 30 ml of methanol. The filtrate and the washed solution were combined and concentrated under reduced pressure, and then, the concentrate was distilled under reduced pressure (73 to 74C, 2.67 kPa) to tive 7.94 g (Isolation yield; 76.6%) of 4-aminomethyltetrahydropyran as colorless liquid. Physical properties of the 4-aminomethyltetrahydropyran are as follows. 1H-NMR (DMSO-d6, delta (ppm)); 1.02 to 1.16 (2H, m), 1.10 to 1.50 (2H, brs), 1.34 to 1.45 (1H, m), 1.56 to 1.61 (2H, m), 2.39 (2H, d, J=6.3Hz), 3.20 to 3.29 (2H, m), 3.81 to 3.86 (2H, m) CI-MS (m/e); 116 (M+1), 99 Example 45 (Synthesis of 4-aminomethyltetrahydropyran) In an autoclave made of stainless equipped with a stirring device, a thermometer and a pressure gauge and having an inner volume of 200 ml were charged 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 100 ml of 22% by weight ammonia methanol solution and 2.0 g (17.0 mmol in terms of a nickel atom) of developed Raney nickel (available from Nikki Chemical Co., Ltd.; sponge nickel N154D), and the mixture was reacted under hydrogen atmosphere (0.51 to 0.61MPa) at 50 to 60C for 5 hours under stirring. After completion of the reaction, insoluble materials were filtered, the filtered material was washed with 30 ml of methanol, and the filtrate and the washed solution were combined. When this solution was analyzed by gas chromatography (Internal standard method), 8.84 g (Reaction yield: 85.3%) of 4-aminomethyltetrahydropyran was found to be formed. Incidentally, bis(4-tetrahydropyranylmethyl)amine which is a by-product was not formed., 4295-99-2

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Patent; Ube Industries, Ltd.; EP1671937; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The a mixture of 3- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy) -4′- ((S)-2-(2-cyclopropylphenyl) pyrrolidin-1-yl) -2′, 3′, 4′, 5′-tetrahydro- [1, 1′-biphenyl] -4-carboxylic acid (650 mg, 1.25 mmol) in DCM (20 mL) was added EDCI (480 mg, 2.50 mmol), triethylamine (630 mg, 6.26 mmol), 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (395 mg, 1.25 mmol) and DMAP (306 mg, 2.50 mmol), the solution was stirred at r.t for 40 h. The reaction solution was washed with H 2O (30 mL3), concentrated and purified by chromatography column on silica (eluent: MeOH/DCM = 0/25 to 1/25) to afford the product (700 mg, 68.5%). MS (ESI, m/e) [M+1] + 817.2. 1H NMR (400 MHz, DMSO-d 6) delta ppm: 11.64 (s, 1H), 8.48 (s, 2H), 7.96 (s, 1H), 7.80-7.40 (m, 5H), 7.30-6.84 (m, 5H), 6.73 (s, 1H), 6.35 (s, 1H), 6.04-5.79 (m, 1H), 3.88-3.81 (m, 2H), 3.32-3.16 (m, 6H), 2.38-1.21 (m, 18H), 0.97-0.84 (m, 2H), 0.72-0.50 (m, 2H). MS (ESI) m/e [M+1] + 763.2. MS (ESI) m/e [M+1] + 805.2

1228779-96-1, The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-65-0, (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step B: 1 -(Tetrahvdropyran-4-yl)methyl-7-chloro-1 /-/-indole-3-carboxylic acid To a solution of 7-chloro-1 /-/-indole-3-carboxylic acid (7.5 g, 38.0 mmol) in di- methylformamide (100 ml) at 10 C under nitrogen was added sodium hydride (60% dispersion in mineral oil, 3.1 g, 76.0 mmol) portionwise over 10 mins, maintaining the temperature below 15 C. The cooling bath was removed and the suspension stirred for 90 mins. Toluene-4-sulfonic acid tetrahydopyran-4-ylmethylester (14.6 g, 53.0 mmol) was added. The mixture was heated at 50 C with stirring for 6 h. Dimethylformamide was removed by evaporation and the residue was dissolved in water (500 ml). The emulsion was washed with dichloromethane (2 x 100 ml). The aqueous phase was acidified to pH 1 using 5 M hydrochloric acid and the precipitate filtered off, washed with water to neutrality and dried to afford 1-(tetrahydropyran-4- yl)methyl-7-chloro-1 /-/-indole-3-carboxylic acid (15.0 g, 51.0 mmol) as a white solid.

101691-65-0, As the paragraph descriping shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; AKZO NOBEL N.V.; WO2007/23143; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1240390-36-6, tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 27 6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-4-(6-isopropyl-5-methylpyridin-2-ylamino)pyridazine-3-carboxamide A mixture of 6-chloro-4-(6-isopropyl-5-methylpyridin-2-ylamino) pyridazine-3-carboxamide (223 mg, 729 mumol, prepared as described in example 25), tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (315 mg, 1.46 mmol) and NMP (4 mL) was stirred at 140 C. for 18 h. The NMP was distilled off using a Kugelrohr apparatus under high vacuum to give a light brown solid. The crude material was dissolved in dichloromethane and MeOH and adsorbed on silica gel, then purified by chromatography (spherical silica 20-45 mum, 11 g, Versaflash from Supelco, eluting with 100% dichloromethane to 88:11.4:0.6 dichloromethane:methanol:NH4OH over 40 min) to give 109 mg of intermediate as a brown solid. This intermediate was dissolved in dichloromethane (2 mL) and TFA (740 mg, 500 muL, 6.49 mmol) was added. The mixture was stirred at room temperature for 16 h. The TFA and the dichloromethane were concentrated in vacuo and the residue obtained was purified by chromatography (spherical silica 20-45 mum, 11 g, Versaflash from Supelco, eluting with 100% dichloromethane to 88:11.4:0.6 dichloromethane:methanol:NH4OH over 40 min) to give a brown solid. The solid was suspended in 0.5 mL heptane and 10 drops of ethanol. The mixture was briefly sonicated and then heated, then cooled and the solvents decanted. The solid residue was dried overnight under high vacuum to give 6-((3R,4R)-3-aminotetrahydro-2H-pyran-4-ylamino)-4-(6-isopropyl-5-methylpyridin-2-ylamino)pyridazine-3-carboxamide (22 mg, 8%) as a brown solid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 11.18-11.31 (m, 1H), 8.26 (s, 1H), 7.95 (br. s., 1H), 7.26 (d, J=8.34 Hz, 1H), 6.55 (d, J=8.08 Hz, 1H), 5.73 (d, J=7.33 Hz, 1H), 5.29 (br. s., 1H), 3.99 (br. s., 1H), 3.90 (d, J=8.08 Hz, 1H), 3.78 (d, J=11.37 Hz, 1H), 3.66 (q, J=7.07 Hz, 1H), 3.57 (d, J=11.37 Hz, 1H), 3.44 (t, J=11.12 Hz, 1H), 3.20 (dt, J=13.33, 6.60 Hz, 1H), 2.97 (br. s., 1H), 2.21 (s, 3H), 1.89 (d, J=11.12 Hz, 1H), 1.61-1.77 (m, 1H), 1.25 (dd, J=6.57, 3.54 Hz, 6H), 1.18 (t, J=7.07 Hz, 1H); LC-MS 386 [M+H]+., 1240390-36-6

The synthetic route of 1240390-36-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hoffman-La Roche Inc.; Hermann, Johannes Cornelius; Kennedy-Smith, Joshua; Lucas, Matthew C.; Padilla, Fernando; Soth, Michael; US2013/178478; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics