Day: November 6, 2020

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.

To a solution of 133 g (1.31 mol) of Compound 23 in pyridine (1.5 L) are added 373 g (1.95 mol) of p-toluenesulfonylchloride portionwise at 10 C. After complete addition the reaction is allowed to warm to room temperature and stirred for 18 h. The reaction is poured onto a stirred mixture of aqueous HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1M aqueous HCl solution (1 L), followed by saturated aqueous NaHCO3 solution (1 L) and is then dried over Na2SO4. Filtration and concentration of the filtrate under reduced pressure gives 300 g of Compound 24 as an orange oil. Yield: 90%, ES-MS: m/z: 257 [M+H], 279 [M+Na]., 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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/71196; (2011); 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

Step 2 {(3R,4R)-4-[7-(5,6-Dimethyl-pyridin-2-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester To a solution of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethyl-pyridin-2-yl)-amide (0.149 g, 0.466 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.121 g, 0.559 mmol) in dioxane (4 mL) was added diisopropylethylamine (0.244 mL, 1.4 mmol). The reaction mixture was heated at 120 C. overnight. The reaction mixture was cooled and then diluted with dichloromethane, washed with aqueous sodium carbonate, then brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was then purified by chromatography (silica, 40 g, 0 to 15% EtOAc in hexanes) to give {(3R,4R)-4-[7-(5,6-dimethyl-pyridin-2-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.105 g, 0.210 mmol, 45%) as a yellow solid. LCMS m/z [M+H]=499.

1240390-36-6, 1240390-36-6 tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate 68077633, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

40191-32-0, Tetrahydro-2H-pyran-4-carbonyl chloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-(1-methoxypropan-2-yl)quinoline-3,4-diamine (for a preparation see Intermediate 2) (9.1 g) in DCM (300 ml) was treated with pyridine (30 ml) and tetrahydro-2H-pyran-4-carbonyl chloride (5.0 ml) and the solution stirred under nitrogen at ambient temperature for 3.5 h and then left standing overnight (ambient temperature, under nitrogen). The volatiles were evaporated in vacuo and the residue partitioned between DCM and water. The organic phase was washed with water ¡Á2 and the combined aqueous extracted with DCM. The combined organic phases were washed with brine, dried (hydrophobic frit) and reduced to dryness in vacuo. The combined aqueous including the brine wash (pH4) was basified with solid sodium hydrogen carbonate and the aqueous extracted with DCM x2. The organic fractions were dried (hydrophobic frit), combined with the previous material and reduced to dryness in vacuo to give a brown foam. This foam was further dried in vacuo, triturated with diethyl ether, the suspension chilled (ice/water bath) and the solid isolated by filtration. The solid was washed with a little diethyl ether and air-dried to give N-(7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-4-((1-methoxypropan-2-yl)amino)quinolin-3-yl)tetrahydro-2H-pyran-4-carboxamide as a beige solid (11.95 g, 100%). [0159] NMR (D6-DMSO): deltaH 9.49 (s, 1H), 8.38 (s, 1H), 7.70 (s, 1H), 7.63 (s, 1H), 5.33 (d, 1H), 3.96-3.90 (m, 6H), 3.43-3.28 (m partially obscured by water, 7H), 2.69 (m, 1H), 2.32 (s, 3H), 2.12 (s, 3H), 1.81-1.67 (m, 4H), 1.19 (d, 3H). LCMS (formate): Rt 0.69 mins, MH+469

40191-32-0, 40191-32-0 Tetrahydro-2H-pyran-4-carbonyl chloride 2795505, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GlaxcoSmithKline LLC; Demont, Emmanuel Hubert; Jones, Katherine Louise; Watson, Robert J.; US2014/171462; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,125552-89-8

To a stirred solution of Intermediate 3 (250 mg, 1 mmol) and 4-(bromomethyl)tetrahydro-2H-pyran (449 mg, 2.51 mmol) in anhydrous MeCN (7 mL)was added dipotassium carbonate (347 mg, 2.51 mmol). The reaction mixture wasstirred overnight at 100C, cooled to RT, filtered through Celite and concentrated under reduced pressure. The resulting material was purified by chromatography using si[ica ge[ (gradient: hexane/EE) to give 1.0 g (76 % yie[d) of the tit[e compound as a co[our[ess oi[.1H NMR (500MHz, CDC[3): 6 [ppm] 8.08 (t, J = 1.4 Hz, 1H), 7.69-7.67 (m, 1H), 7.57 (dd, J = 2.5, 1.4 Hz, 1H), 7.53 – 7.51 (m, 1H), 4.05 – 4.00 (m, 2H), 3.94 (s, 3H),3.92 (d, J = 6.5 Hz, 2H), 3.49 – 3.42 (m, 2H), 2.53 – 2.52 (m, 3H), 2.14 – 2.03 (m,1H), 1.80- 1.75 (m, 2H), 1.53- 1.43 (m, 2H).LCMS (Ana[ytica[ Method A) Rt = 1 .45 min, MS (ESipos): m/z = 348 (M+H).

125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

127956-11-0, Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 2 (1.58 g, 10 mmol) and ammonium acetate (2.3 g, 30 mmol) in of MeOH (20 mL) was stirred overnight at room temperature. The mixture was concentrated under vacuum, dichloromethane (100 mL) and water (20 mL) were added, and the separated organic layer was dried over sodium sulfate and concentrated in vacuo. The crude product 3 was dissolved in 20 mL of CH3CN and treated with 2,2,2-trichloro-acetyl isocyanate (3.76 g, 20 mmol) and the mixture was stirred for 30 minutes. The resulting solid was collected by filtration and dissolved in NH3 in MeOH (8 mL, 7 N), the mixture was heated at 70C. After cooling to room temperature, a solid formed and was collected by filtration to give compound 4 (1.2 g, 71%). 1H NMR (300 MHz, DMSO-d6): delta 10.98 (br, 2H), 4.19 (s, 2H), 3.76 (t, J = 5.4 Hz, 2H), 2.38 (t, J = 5.4 Hz, 2H).

127956-11-0, 127956-11-0 Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate 14666555, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ZHOU, Han-Jie; PARLATI, Francesco; WUSTROW, David; WO2014/15291; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A flask was charged with AlCl3 (78.8 mmol, 10.5 g, 2.3 equiv) and dry CH2Cl2 (25 ml) under calcium chloride guard tube and the formed suspension was stirred on ice bath. Subsequently, a solution of glutaric anhydride 10 (34.3 mmol, 3.91 g) in dry CH2Cl2 (15 ml) was added dropwise (t < 7 C). The resulting mixture was stirred on ice bath for 30 minutes and bromobenzene 11b (34.3 mmol, 5.39 g, 1.0 equiv) was carefully added afterwards. The cooling bath was removed and the mixture was stirred at room temperature for 19 hours, then it was poured into ice water (15 ml), acidified with conc. H2SO4 (10 ml), the aqueous layer was extracted with ethyl acetate (1 x 100 ml, 2 x 50 ml), the combined organics were dried over Na2SO4, filtered and concentrated. The crude product was dissolved in ethyl acetate and the resulting solution was added dropwise to a vigorously stirred cold hexanes (1 L). The precipitate was filtered off and dried to provide 5-(4-bromophenyl)-5-oxopentanoic acid (7.93 g, 85%) as a yellow powder;2 mp 125-127 C; 1H NMR (300 MHz, CDCl3): delta = 2.07 (m, 2H), 2.50 (t, J = 7.2 Hz, 2H), 3.04 (t, J = 7.2 Hz, 2H), 7.60 (m, 2H), 7.82 (m, 2H). 5-(4-Bromophenyl)-5-oxopentanoic acid (25.0 mmol, 6.78 g), paraformaldehyde (86.3 mmol, 2.59 g, 3.4 equiv) and piperidine (0.57 ml, 0.24 equiv) were dissolved/suspended in pyridine (42 ml) and stirred at 70 C for 21 hours. Afterwards, the mixture was poured into 1M H2SO4 (200 ml)/conc. H2SO4 (15 ml), the aqueous layer was extracted with ethyl acetate (1 x 150 ml, 2 x 100 ml), the combined organics were washed with half-saturated brine (300 ml), dried over Na2SO4, filtered and concentrated. The crude product was crystallized from ethyl acetate to yield 4-(4-bromobenzoyl)pent-4-enoic acid 9b (3.93 g, 56%) as an orange-yellow solid; mp 127-128 C; 1H NMR (300 MHz, CDCl3): delta = 2.63 (t, J = 6.9 Hz, 2H), 2.80 (t, J = 6.9 Hz, 2H), 5.67 (s, 1H), 5.95 (s, 1H), 7.60 (m, 4H); 13C NMR (75 MHz, CDCl3): delta = 27.2, 32.6, 127.3, 127.4, 131.0, 131.6, 136.3, 145.8, 178.9, 196.6. 108-55-4, 108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Sivak, Ivan; Berke?, Du?an; Ko?i?ek, Jozef; Kolarovi?, Andrej; Tetrahedron Letters; vol. 57; 10; (2016); p. 1079 – 1082;,
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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

A mixture of methyl 6-(5′-bromo-2′-hydroxy-2-biphenylyl)-2-pyridinecarboxylate (200mg, 0.52mmol), tetrahydro-2H-pyran-4-ylmethyl-4-methylbenzene sulphonate (430mg, 1.5mmol) and potassium cabonate (200mg) in dimethylformamide (4ml) was heated to reflux for 3 hours under nitrogen. The reaction mixture was then filtered through celite, washed with ethyl acetate (10mls) and evaporated to an oil which was flash chromatographed eluting with diethyl ether/isohexane (1/5). The product was dissolved in methanol (10ml), treated with 2N sodium hydroxide (2ml) and heated at 70C for 15min. The solution was evaporated and partitioned between water and ethyl acetate. After drying with anhydrous sodium sulphate the ethyl acetate solution was evaporated to give the title compound (130mg). LC/MS [M+H] 470.3, 471.4, Rt=3.65min., 101691-65-0

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

Reference£º
Patent; GLAXO GROUP LIMITED; WO2005/108369; (2005); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 3 – SYNTHESIS OF METHYL 3-ISOBUTYL-GLUTARATE (III) A 1 L three-necked round-bottom flask, under nitrogen atmosphere, is loaded with 3-isobutylglutaric anhydride (50.0 g; 0.290 mol) of formula (II), methanol (500 ml) and triethylamine (29.3 g; 0.290 mol); the resulting solution is kept under stirring at room temperature for about 16-18 h. After completion of the reaction, the solvent is evaporated off, the mixture is taken up with water (200 ml), acidified to pH 3-4 with 37% hydrochloric acid and extracted with toluene (3×150 ml). The combined organic phases are evaporated under reduced pressure, to obtain a pale yellow oil (58.6 g; yield: 95%). 1H-NMR (300 MHz, CDCl3, 28C): delta 3.65 (s, 3H); 2.40 (m, 5H); 1.60 (m, 1H); 1.20 (m, 2H); 0.90 (d, 6H)., 185815-59-2

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

Reference£º
Patent; Dipharma Francis S.r.l.; EP1992609; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

951127-25-6, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

951127-25-6, General procedure: Compound 3 (101 mg, 0.31 mmol) and amines 10a-g (0.32 mmol) were dissolved in trifluoroacetic acid (0.45 mL, 6.1 mmol) at 0 C and stirred at 0 C for 1 h. To the resulting solution, DMAC (1.3 mL,14.0 mmol) and TEA (0.42 mL, 3.0 mmol) were added slowly and the internal temperature was maintained below 15 C. The mixture was then cooled to 0 C, treated with STAB (91 mg, 0.43 mmol),and stirred at 0-2 C for 5 h. Eventually the pH of the reaction was brought to 9 with conc. aq. NH3, and the resulting suspension was filtered. The filtrate was diluted with water (15 mL), extracted ethyl acetate for several times. Combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, DCM: MeOH = 20:1) to yield the products11-14. From compound 10a (30 mg, 0.32 mmol), according to general procedure A, compound 11 (lightyellow oil, 61 mg, 0.20 mmol, 65 %) was obtained. Rf 0.6 (20:1, dichloromethane : methanol); [alpha]D -1.02(c 0.275, CHCl3); HPLC tR 2.63 min; 1H NMR (500 MHz, CDCl3) delta 7.23 – 7.13 (m, 3H, ArH), 7.05 – 6.95(m, 2H, ArH), 6.76 – 6.71 (m, 1H, ArH), 6.70 – 6.68 (m, 1H, ArH), 6.68 – 6.65 (m, 1H, ArH), 4.33 (ddd,J = 11.2, 4.6, 2.1 Hz, 1H, H-5), 4.25 (d, J = 9.4 Hz, 1H, H-1), 3.74 (tt, J = 10.9, 4.3 Hz, 1H, H-4), 3.14 (t,J = 10.9 Hz, 1H, H-5?), 2.97 – 2.91 (m, 1H, H-2), 2.52 (dtd, J = 12.1, 4.0, 2.3 Hz, 1H, H-3), 1.67 (s, 2H,NH2), 1.36 (q, J = 11.6 Hz, 1H, H-3), peaks of NH was missing; 13C NMR (151 MHz, CDCl3) delta 160.12 -158.35 (m, ArC), 157.52 – 155.64 (m, ArC), 146.67 (ArC), 129.61 (2C, ArC), 128.60 (dd, J C-C-F = 16.1,7.4 Hz, ArC), 118.03 (ArC), 116.68 (dd, J C-C-F = 25.6, 8.5 Hz, ArC), 116.37 (dd, J C-C-F = 24.2, 8.7 Hz,ArC), 114.83 (dd, J = 24.6, 4.2 Hz, ArC), 113.16 (2C, ArC), 79.35 (C-1), 72.09 (C-5), 53.20 (C-2), 49.08(C-4), 40.73 (C-3); HRMS (ESI+) calcd. For C17H19F2N2O+ 305.1460, found 305.1455.

The synthetic route of 951127-25-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Li, You; Liu, Tongchao; Li, Chungang; Xiong, Bing; Zhao, Dongmei; Cheng, Maosheng; Chen, Guohua; Shen, Jingkang; Chen, Yue-Lei; Synthetic Communications; vol. 47; 4; (2017); p. 357 – 363;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4295-99-2

In a 1 L glass flask equipped with a stirrer, a thermometer, a gas inlet tube and a reflux condenser,100.06 g (900.3 mmol) of 4-cyanotetrahydropyran, 28.83 g (899.8 mmol) of methanol and 327 g of methylene chloride were added,While blowing hydrogen chloride gas,The mixture was allowed to react at 0 to 7 C. for 7 hours with stirring. After completion of the reaction, the reaction solution was concentrated,421 g of tert-butyl methyl ether was added, and the mixture was stirred at 3 to 10 C. for 1 hour. The obtained crystals were filtered,The filtrate was dried to obtain 157.68 g of methyl tetrahydropyran-4-imidate hydrochloride (isolation yield: 98%).

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UBE INDUSTRIES LIMITED; NAKATANI, RYO; IWATA, TOMOCHIKA; FUKUHARA, YASUAKI; MOTOYAMA, TAKAHIRO; (34 pag.)JP6183053; (2017); B2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics