Category: Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31608-22-7,2-(4-Bromobutoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

2-[4-(2,3-Difluorophenoxy)-butoxy]-tetrahydropyran (20) To a solution of 2-(4-bromobutoxy)-tetrahydropyran (18) (1 equi.) and commercially available 2,3-difluorophenol (19) (1 equi.) in DMF (3 mL/mmole), cesium carbonate (1.25 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile gave 2-[4-(2,3-difluorophenoxy)-butoxy]-tetrahydropyran(20), as a white solid (84%)., 31608-22-7

As the paragraph descriping shows that 31608-22-7 is playing an increasingly important role.

Reference£º
Patent; Wand, Michael; Gough, Neil; Chen, Xin Hua; US2003/17278; (2003); 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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

Step 2: 2-Methoxy-1-(tetrahydro-2H-pyran-4-yl)ethanoneA dry 50 mL flask under nitrogen was charged with magnesium (197 mg, 8.11 mmol) and a crystal of iodine. The solids were stirred vigorously while being warmedwith the heat gun to aerosolize the iodine. Upon cooling to room temperature, it was treated with THF (4 mL). The mixture was warmed with a heat gun and treated with a solution of 4-bromotetrahydro-2H-pyran (0.678 mL, 6.08 mmol) in THF (4 mL) dropwise via a dry addition funnel. When addition was complete, the mixture was placed in a preheated oil bath, and the mixture held at reflux for 30 mm. After cooling to room temperature, the solution was transferred to a stirred solution of N,2-dimethoxy-N- methylacetamide (270 mg, 2.03 mmol) in THF (12 mL) at -78 C. After stirring for 5 mm, the ice bath was removed and the reaction allowed to warm to room temperature. The reaction was placed in a 0 C bath, quenched by addition of sat. aq. ammoniumchloride, concentrated, diluted with EtOAc, washed with water, then brine, dried over magnesium sulfate, filtered, and concentrated to give 260 mg (81%) as clear oil. Material was used without purification. ?H NMR (400 MHz, CDC13) oe 4.1 1(s, 2H), 4.05-4.0(m, 2H), 3.5-3.44(m, 2H), 3.45(s, 3H), 2.8(m, 1H), 1.64(m, 2H), 1.32(m, 2H).

25637-16-5, The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Tetrahydropyran – Wikipedia
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

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-2/-/-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 with dichloromethane (2 x 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 eluting with 50% dichloromethane in n-heptane to yield a further quantity of toluene-4-sulfonic acid tetrahydro-pyran-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; AKZO NOBEL N.V.; WO2007/23143; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of crude 9-hydroxy-6-isobutyi- 1 0-methoxy-2-oxo-7H-pyrido [2,1 -a]phthalazine-3-carboxylic acid (60 mg) in DMF (3 mL) was added potassium carbonate (74.2mg, 537 jimol) and 4-(iodomethyl)tetrahydro-2H-pyran (91 mg, 402 iimol), The mixture washeated at 100 C with stirring for 3 hrs, and then cooled to rt, To the above mixture was addedwater (3 mL) and sodium hydroxide (10.7 mg, 268 imol). The resulting mixture was stirred at rtfor 2 hrs, and then acidified with 6 M hydrochloric acid. The mixture was partitioned betweenbrine and DCM, The organic layer was separated and concentrated under reduced pressure. Theresidue was purified by prep-HPLC to give 6-isobutyl- 1 0-rnethoxy-2-oxo-9-(tetrahydropyran-4-ylmethoxy)-7H-pyrido [2,1 -a]phthalazine-3 -carboxylic acid (5 mg), ?H NMR (400MHz, CDC13)oe ppm 8.60 (s, 1H), 7.20 (s, 1H), 7.04 (s, 1H), 6.72 (s, 1H), 4.36 – 4.16 (m, 2H), 4.08 – 4.01 (m,2H), 3.94 (s, 3H), 3.92 (d, 2H), 3.52 – 3.43 (m, 2H), 2.53 (d, 2H), 2.24 – 2.19 (m, 1H), 2.05 – 1.99(m, 1H), 1.69-1.60 (m, 2H), 1.54 – 1.42 (m, 2H), 0.96 (d, 6H). MS obsd. (ESIj [(M+H)]: 443., 101691-94-5

101691-94-5 4-(Iodomethyl)tetrahydro-2H-pyran 2795507, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; WANG, Yongguang; YANG, Song; (47 pag.)WO2017/17043; (2017); A1;,
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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

Intermediate 221,1-Dimethylethyl 2-(tetrah dro-2H-pyran-4-yl)hydrazinecarboxylateTetrahydro-4H-pyran-4-one (9.69 g, 97 mmol) was added to a solution of 1,1- dimethylethyl hydrazinecarboxylate (14.07 g, 106 mmol) in methanol (100 mL) and stirred at room temperature for 3 h. The solvent was removed in vacuo, and the crude residue was suspended in acetic acid (140 mL). Next added sodium cyanoborohydride (6.69 g, 106 mmol) in portions over 3 minutes. The contents were stirred at room temperature for 60 h. The solvent was removed in vacuo, and the crude residue was suspended in DCM (100 mL). The reaction mixture was adjusted to pH 7 with 6N NaOH. The layers were separated, and the aq. layer extracted with DCM. The combined organic layers were washed with saturated NaHC03, and brine. The organic layer was dried over MgS04, filtered, and concentrated in vacuo to afford the product as a solid, 18.4 g (88%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.22 (m, 2 H), 1.39 (s, 9 H), 1.43 – 1.48 (m, 1 H), 1.59 – 1.69 (m, 2 H), 2.82 – 2.98 (m, 1 H), 3.20 – 3.32 (m, 2 H), 3.80 (d, J=l 1.62 Hz, 2 H), 4.36 (br. s., 1 H), 8.07 – 8.34 (m, 1 H)., 29943-42-8

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

Reference£º
Patent; GLAX0SMITHKLINE LLC; BURGESS, Joelle, Lorraine; JOHNSON, Neil, W.; KNIGHT, Steven, David; LAFRANCE, Louis, Vincent, III; MILLER, William, H.; NEWLANDER, Kenneth, Allen; ROMERIL, Stuart, Paul; ROUSE, Meagan, B.; SUAREZ, Dominic; TIAN, Xinrong; VERMA, Sharad, Kumar; WO2013/39988; (2013); 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

Compound 294.1. (E)-3-(Dimethylamino)-l-(tetrahydro-2H-pyran-4-yl)prop-2- en-l-one. To a sealed tube were added l-(tetrahydro-2H-pyran-4-yl)ethanone (3.00 g, 23.4 mmol) and DMF-DMA (6.2 mL, 46.8 mmol). The reaction mixture was heated at 100 C overnight. The resulting mixture was concentrated under reduced pressure to afford 4.00 g (crude) of the title compound as light yellow oil.

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

Reference£º
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); 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.1172623-99-2,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

1H (11.53 g, 35.03 mmol) was dissolved in dichloromethane (130 mL) and cooled to 0 C.Dess-Martin periodinane (29.72 g, 70.06 mmol) was added portionwise to the reaction mixture and allowed to react to room temperature for 4 hours. Cool down to 0 C,Saturated sodium hydrogen carbonate solution (60 mL) was added dropwise to the reaction mixture, stirred for 20 minutes, and filtered.The filtrate was allowed to stand for stratification, and the aqueous phase was extracted with methyl tert-butyl ether (60 mL ¡Á 3).Wash with saturated sodium bicarbonate solution (30 mL ¡Á 2), dry over anhydrous sodium sulfate, and then concentrated by filtration and eluted by column chromatography ( petroleum ether / ethyl acetate (v/v) = 10:1-4:1 ),The white crystalline powder Intermediate 1 (10.85 g, yield 94.7%) was obtained., 1172623-99-2

The synthetic route of 1172623-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Fan Jiang; Feng Jianchuan; Peng Fei; Chen Qingping; (45 pag.)CN105085530; (2019); B;,
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.1240390-36-6,tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Step 2 {(3R,4R)-4-[7-(Pyrazolo[1,5-a]pyridine-3-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 pyrazolo[1,5-a]pyrimidin-3-ylamide (0.154 g, 0.466 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.111 g, 0.513 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% MeOH in dichloromethane) to give {(3R,4R)-4-[7-(pyrazolo[1,5-a]pyridine-3-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.137 g, 0.268 mmol, 57%) as a yellow solid. LCMS m/z [M+H]=511.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

1228779-96-1, Compound 17-3 was dissolved in dichloromethane, (3 eq) EDCI, (0.3 eq) DMAP was added, and stirred at room temperature for half an hour, then compound 1-5 (0.8 eq) was added.It is then reacted at room temperature for 6-8 hours. After the reaction is completed, the reaction is quenched with water.Extract three times with dichloromethane, and combine the organic phases with saturated brine.After drying anhydrous sodium sulfate, mix the sample on the column.CH2Cl2: MeOH = 100:1 – 30:1 gave compound S17.

As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

Reference£º
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Tan Wenfu; Liu Xiaohua; Huang Wenjing; Zhang Yu; Yang Jun; (37 pag.)CN110143974; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

344329-76-6, Tetrahydro-2H-pyran-4-carboxamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 87 A^-[10,ll-dichloro-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02’6]dodeca- l(12),6,8,10-tetraen-3-yl]oxane-4-carboxamide (ABR 239441) To a stirred solution of oxane-4-carboxamide (500 mg, 3.87 mmol) in DMF (15 mL) was added pyridine (312 mu, 3.87 mmol) followed by ethyl 3,3,3-trifluoro-2-oxopropanoate (658 mg, 3.87 mmol) at room temperature under argon. The reaction mixture was stirred at room temperature for 1 h and then thionyl chloride (422 mu, 5.81 mmol) was added. The reaction was stirred for a further 16 h and was then concentrated. The acyl intermediate that remained was dissolved in DMF (5 mL) under argon. A solution of 5,6-dichloro-lH-l ,3-benzodiazol-2-amine (587 mg, 2.90 mmol) in DMF (7 mL) and triethylamine (861 mu, 6.19 mmol) were added and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2 x 15 mL). The combined organic extracts were washed with brine, dried (MgSO^, filtered and concentrated. The crude product was purified by silica chromatography. Further purification was carried out by trituration in DCM/MeOH and then pentane to afford the title compound (20 mg, 1percent).

344329-76-6, The synthetic route of 344329-76-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ACTIVE BIOTECH AB; WELLMAR, Ulf; LIBERG, David; EKBLAD, Maria; BAINBRIDGE, Marie; EAST, Stephen; HARGRAVE, Jonathan; PREVOST, Natacha; WO2015/177367; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics