Heterocyclic Building Blocks-Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.110238-91-0,Methyl tetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

Into a 100 mL round-bottom flask, were placed a solution of compound 19.1 (200 mg, 1.39 mmol, 1.00 equiv) in THF (50 mL) and LiA1H4 (63 mg, 1.66 mmol, 1.20 equiv). Reaction was stirred for 3 h at room temperature and then quenched using NaSO4.10H20. The solids were filtered out. Resulting solution was concentrated under vacuum furnish 150 mg (crude) of oxan-4-ylmethanol as a yellow solid.

110238-91-0, 110238-91-0 Methyl tetrahydro-2H-pyran-4-carboxylate 2773520, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); 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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

A solution of tetrahydro-4H-pyran-4-one (25 g, 250 mmol) and toluenesulfonylmethyl cyanide (53.7 g, 275 mmol) dissolved in ethylene glycol dimethylether (1 L) was cooled to 0 C. Added dropwise over 30 min was a solution of potassium t-butoxide (56 g, 500 mmol) dissolved in t-butanol (350 mL) and ethylene glycol dimethylether (150 mL). After stirring the resulting mixture for 3 h at room temp, diethyl ether (1 L) was added and the organic phase was washed with saturated aqueous NaHCO3. The organic phase was dried (Na2SO4) and concentrated. The residue was distilled at 39 C. 1.7 mm Hg to give the title compound as colorless oil (10.87 g, 39% yield). 1H NMR (300 MHz, CDCl3) delta: 3.91-3.83 (2H, m), 3.61-3.54 (2H, m), 2.89-2.80 (1H, m), 1.97-1.78 (4H, m).

29943-42-8, The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bristol-Myers Squibb Company; US2008/306051; (2008); 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.65412-03-5,4-(2-Aminoethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylpropanoic acid (100 mg, 0.2570 mmol) , 2- (tetrahydro-2H-pyran-4- yl) ethan-1-amine (40 mg, 0.3085 mmol) , HATU (146 mg, 0.3856 mmol) , DIPEA (99 mg, 0.7712 mmol) in DMF (3 mL) was stirred at rt for 3 hours. The reaction mixture was poured into H 2O (10 mL) and extracted with EtOAc (15 mL x 3) . The combined organic layers were washed with brine, dried over Na 2SO 4, concentrated and purified by column chromatography (DCM/MeOH=40: 110: 1) to give the product (62 mg, 48.2%) . 1HNMR (400 MHz, DMSO-d6) delta 8.24 (s, 1H) , 8.00 (s, 2H) , 7.95 (d, J = 0.9 Hz, 1H) , 7.53 (t, J = 5.6 Hz, 1H) , 7.34 -7.20 (m, 4H) , 7.15 (dd, J = 8.0, 1.4 Hz, 2H) , 6.74 (dd, J = 3.4, 1.8 Hz, 1H) , 3.76 -3.66 (m, 2H) , 3.15 (q, J = 6.6 Hz, 2H) , 3.04 (dd, J = 23.4, 11.6 Hz, 2H) , 2.28 (s, 3H) , 1.51 -1.39 (m, 2H) , 1.37 -1.27 (m, 2H) , 1.26 -1.17 (m, 1H) , 1.02 (ddd, J = 23.9, 12.0, 4.2 Hz, 2H) . MS: M/e 501 (M+1) +., 65412-03-5

As the paragraph descriping shows that 65412-03-5 is playing an increasingly important role.

Reference£º
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (152 pag.)WO2019/196803; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5, Tetrahydropyranyl-4-acetic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of 0.55 g of LiAlH4 (13.9 mmol) in THF (10 mL) is added dropwise a solution of 2 g (13.9 mmol) of Compound 17 in THF (10 mL) under nitrogen atmosphere. Upon complete addition, the reaction is stirred at room temperature for 18 h. The reaction is cooled in an ice-bath and quenched with addition of 1M aqueous NH4Cl solution (2 mL). The resulting precipitate is removed by filtration through Celite and is rinsed with ethyl acetate (3¡Á100 mL). The filtrate is dried over Na2SO4, filtered and concentrated under reduced pressure to afford 1.63 g of Compound 18 as a colorless oil. Yield: 90%; ES-MS m/z 131 [M+H]; 1H-NMR (500 MHz, CHLOROFORM-d) delta ppm 1.29 (2H, qd, J=12.08, 4.04 Hz), 1.50 (2H, qd, J=6.71, 1.37 Hz), 1.55-1.73 (3H, m), 1.95-2.07 (1H, m), 3.37 (2H, t, J=11.83 Hz), 3.66 (2H, t, J=6.03 Hz), 3.92 (2H, dd, J=11.44, 4.12 Hz)., 85064-61-5

85064-61-5 Tetrahydropyranyl-4-acetic acid 2773575, 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

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 179: N-(4-methoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)ethanamine To a stirred solution of 1-(tetrahydro-2H-pyran-4-yl)ethanone (3.2 g, 24.97 mmol) in DCM) (50 mL was added (4-methoxyphenyl)methanamine (6.87 g, 50.1 mmol). The resulting yellow solution was stirred for 4.5 h and sodium triacetoxyborohydride (10 g, 48.6 mmol) added. The white suspension was stirred. The reaction mixture was partitioned between DCM and aq. sat. NaHCO3. The organic layer was removed and the aqueous extracted 3 times with DCM. The combined organic phases were passed through a hydrophobic frit and concentrated in vacuo to give a yellow oil. The oil was dissolved in DCM, purified by silica gel chromatography eluting with EtOAc:EtOH (7.5 – 25%) and evaporated in vacuo to give the title compound as a yellow oil. The total yield of the reaction was 80%. LCMS (System A): tRET = 1.27 min, MH+ = 366.

137052-08-5, The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BIT, Rino Antonio; BROWN, John Alexander; HUMPHREYS, Philip G.; JONES, Katherine Louise; (240 pag.)WO2016/146738; (2016); 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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

137052-08-5, Under nitrogen protection,(R) -MeCBS (718.3 mL, 1 M solution in toluene) was added to a solution of borane dimethyl sulfide (718.3 mL, 7.183 mol) in tetrahydrofuran (4.6 L) at -10 to 0 C.Maintain low temperature conditions,Compound 15 (920 g, 7.183 mol) was added dropwise to the reaction system.After completion of the dropwise addition,The reaction system was stirred at 0 to 5 C for 10 minutes.(2N, 4L) was added slowly at -5 to 0 C to quench the reaction,After stirring for 6 hours, sodium chloride was added until saturation,Methyl tert-butyl ether (2 L) was added and stirred for 5 minutes,The filter cake was rinsed with methyl tert-butyl ether (2 L).The filtrate was allowed to stand,The aqueous phase was extracted with methyl tert-butyl ether until the desired product was not detected in the aqueous phase.The organic phases were combined,And washed with saturated brine (5 L)Dried over anhydrous sodium sulfate,Concentration by filtration afforded crude compound 16 (846 g) as a pale yellow oil,Without further purification,Can be directly used for the next reaction,e.e. value of the compound 16 of Example 10 derived by the reaction was carried out by.

As the paragraph descriping shows that 137052-08-5 is playing an increasingly important role.

Reference£º
Patent; Medchemexpress China Co., Ltd.; Wang, Guangyong; Li, Chaoping; Zhou, Zhiguo; Gao, Qiang; Zheng, Baofu; (12 pag.)CN105669647; (2016); A;,
Tetrahydropyran – Wikipedia
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

2.0 mmol of the compound 5-hydroxy-2,3-dihydro-[1,4]dioxane[2,3-f]quinazolin-10(7H)-one represented by the formula (8) was dissolved in 15 ml of DMF. Add potassium carbonate (550 mg, 4.0 mmol) at room temperature for half an hour, slowly add 3.0 mmol of 4-chlorotetrahydro-2H-pyran to the system, heat to 80 C, react for 6-8 h, and check the progress of the reaction by TLC. After the completion of the reaction, the mixture was poured into 30 ml of ice water and suction filtered to give 5-((tetrahydro-2H-pyran-4-yl)oxy)-2,3-dihydro-[1,4]dioxane [2,3-f]quinazolin-10(7H)-one, yield: 75%., 1768-64-5

1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Beijing University of Technology; Hu Liming; Fan Haoru; Wei Dengshuai; Zeng Chengchu; (19 pag.)CN109776551; (2019); 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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

To a solution of tetrahydro-pyran-4-one (1.3 kg, 12.98 mol) and carbonic acid dimethyl ester (1 1 .69 kg, 129.8 mol) was added solid potassium te/t-butoxide (1 .89 kg, 16.08 mol) in portions at -10C over 2 h under nitrogen protection. The suspension was stirred at room temperature 10 h after the addition. LCMS (215nm) indicated that tetrahydro-pyran- 4-one had been completely consumed. The reaction was acidified by HCI (2 N) to pH 6~7 and then the phases were separated. The organic phase was washed with water (3 Lx2) and the combined aqueous phases were extracted with MTBE (2.5 Lx2). The combined organic phase was concentrated under reduced pressure at 25C to remove most of MTBE. The residue was distilled out by oil pump (-200 Pa) at 74 C to give the title compound as colorless oil (545 g, 26.3%). CHN analysis: calculated (results). C 53.16 (53.10), H 6.37 (6.245), N 0.00 (0.00)., 29943-42-8

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; CHEN, Christine Hiu-Tung; CHIN, Noel Chin; DIPIETRO, Lucian V.; FAN, Jianme; PALERMO, Mark G; SHULTZ, Michael David; TOURE, Bakary-Barry; WO2013/8217; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

61363-56-2, 2H-Pyran-3,5(4H,6H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 29 5-(3-cyanophenyl)-5,10-dihydro-1H,3H-dipyrano[3,4-b:4,3-e]pyridine-4,6(7H,9H)-dione A mixture of tetrahydropyran-3,5-dione (Terasawa, J. Org. Chem. (1977), 42, 1163-1169) (0.27 g, 2.4 mmol), 3-cyanobenzaldehyde (0.54 g, 2.9 mmol) and the product from Example 11C (0.27 g, 2.4 mmol) in ethanol (3 mL) was heated to 80 C. for 60 hours, cooled and concentrated. The residue was purified by chromatography on silica gel (5% methanol in methylene chloride) to provide a product which was dissolved in 1:5 methanol/methylene chloride, filtered, concentrated on a steam bath to remove the methylene chloride and allowed to stand at ambient temperature for 16 hours. The resulting solid was collected by filtration, washed with methanol and dried to provide the title compound (0.062 g). mp>260; MS (ESI(+)) m/z 323 (M+H)+; MS (ESI(-)) m/z 321 (M-H)-; 1H NMR (DMSO-d6) delta 4.05 (s, 4H), 4.51 (AB q, 4H), 4.99 (s, 1H), 7.48 (m, 1H), 7.54-7.64 (m, 2H), 10.12 (bs, 1H); Anal. Calcd for C18H14N2O4: C, 67.08; H, 4.38; N, 8.69. Found: C, 66.76; H, 4.67; N, 8.56., 61363-56-2

61363-56-2 2H-Pyran-3,5(4H,6H)-dione 325287, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Abbott Laboratories; US6191140; (2001); B1;,
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.

a) Preparation of c-(tetrahydro-pyran-4-yl)-methylammonium acetate A cold (ice water bath) solution of tetrahydro-4H-pyran-4-one (7.5 g, 75 mmol) and tosylmethylisocyanide (16.05 g, 82.4 mmol) in DME (125 ml) was treated with a suspension of potassium t-butoxide (16.8 g, 150 mmoles) in t-butyl alcohol (250 ml). The reaction mixture was stirred at room temperature for 31/2 hours, and then diluted with ether (250 ml). The mixture was successively washed with water and brine, then dried over sodium sulfate, filtered, and concentrated. The crude product was purified by short path distillation under high vacuum to give the nitrile as colorless oil (2.98 g). This material was dissolved in 1M borane/tetrahydrofuran (THF) (134 ml, 134 mmol) and stirred at rt overnight. Excess borane was quenched by adding methanol (rt, 1 h), and the mixture was concentrated to dryness. The residue was dissolved in 4N HCl/dioxane, stirred at rt for 1 h and then concentrated under reduced pressure. The solid residue was triturated with ether and collected by suction filtration. A suspension of this material (1.81 g, 11.9 mmol) in THF (30 ml) was treated with 1N NaOH (11.9 ml, 11.9 mmol) at rt for ? h. The THF was removed by distillation and the aqueous solution was saturated with NaCl then extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was treated with acetic acid (0.68 ml, 11.9 mmol) to provide, after drying in a vacuum oven, c-(tetrahydro-pyran-4-yl)-methylammonium acetate (1.71 g).

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

Reference£º
Patent; Chen, Li; Chen, Shaoqing; Michoud, Christophe; US2006/63804; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics