Heterocyclic Building Blocks-Tetrahydropyrans

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 tetrahydro-2H-pyran-4-ol (20 g ) in tetrahydrofuran (150 mL) and triethylamine (28.5 mL) is slowly added methanesulfonyl chloride (15.5 mL), while keeping the temperature below 30C. The mixture is stirred for 12 hours at room temperature. The precipitate is filtered off and washed twice with tetrahydrofuran. The combined organic phases are concentrated and partitioned between ethyl acetate and water. The organic phase is dried (Na2SO4) and concentrated to give the title compound. Yield: 29.4 g; TLC: rf = 0.36 (silicagel, petrole ether/ethyl acetate 1 :1 ); Mass spectrum (ESI+): m/z = 198 [M+NH4]+., 2081-44-9

As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144098; (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

General procedure: The requisite methyl ketone (1equiv), (R)-2-methylpropane-2-sulfinamide (1.5equiv), and Ti(OEt)4 (technical grade, 20% Ti, ?2equiv) in THF (1M), were stirred at reflux for 24-48h. The reaction mixture was cooled to RT and then added to an equal volume of ice water. EtOAc was added and the mixture was stirred vigorously for 15 min after which it was filtered through a pad of Celite. The filter cake was washed with EtOAc. The filtrate was then washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography or triturated with ether to provide the (R)-tert-butanesulfinyl ketimine.

137052-08-5, 137052-08-5 1-(Tetrahydro-2H-pyran-4-yl)ethanone 9877365, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Gilbert, Eric J.; Brunskill, Andrew; Cai, Jiaqiang; Cai, Yaxian; Chu, Xin-Jie; Dai, Xing; Hao, Jinsong; Kuethe, Jeffrey T.; Lai, Zhong; Liu, Hong; Mu, Cuizhi; Qi, Yan; Scott, Jack D.; Taoka, Brandon; Truong, Quang; Walsh, Shawn P.; Wu, Wen-Lian; Cumming, Jared N.; Tetrahedron; vol. 72; 40; (2016); p. 6011 – 6020;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1172623-99-2, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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, 1172623-99-2 tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate 86713019, aTetrahydropyrans compound, is more and more widely used in various fields.

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

388109-26-0, Ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Part D. Preparation of (R)-5-(1-Phenyl-ethylamino)-3,6-dihydro-2H-pyran-4-carboxylic acid ethyl ester A solution of 3-oxo-tetrahydro-pyran-4-carboxylic acid ethyl ester (3.03 g, 17.6 mmol), R-(+)-alpha-methylbenzylamine (2.35 g, 19.4 mmol) and p-toluenesulfonic acid hydrate (67 mg, 230 mumol) in benzene (60 mL) was heated at reflux under a Dean-Stark trap for 16 h. The cooled mixture was concentrated in vacuo to provide the product as a yellow oily semisolid (5.05 g), used without further purification. 1H NMR (300 mHz, CDCl3) delta 8.97 (bd, J=7.3 Hz, 1H), 7.3-7.2 (m, 5H), 4.41 (m, 1H), 4.30 (d, J=16.1 Hz, 1H), 4.18 (q, J=7.3 Hz, 2H), 3.91 (d, J=16.1 Hz, 1H), 3.64 (m, 2H), 2.34 (m, 2H), 1.48 (d, J 6.5 Hz, 3H), 1.30 (t, J 7.3 Hz, 3H).

388109-26-0, The synthetic route of 388109-26-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ko, Soo S.; Pruitt, James R.; Wacker, Dean A.; Batt, Douglas G.; US2003/32654; (2003); A1;,
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

Example 7 Preparation of 1-(4-tetrahydropyranyl)but-1-en-3-one 10.8 g (400 mmol) of Mg turnings are introduced into 30 ml of tetrahydrofuran containing a catalytic amount of iodine, and 5 ml of 4-chlorotetrahydropyran are added. The mixture is warmed to 50 C., and 45.2 g (375 mmol) of 4-chlorotetrahydropyran, dissolved in 120 ml of tetrahydrofuran, are added dropwise at such a rate that the internal temperature does not exceed 70 C. The mixture is stirred for a further 1 hour and subsequently cooled to room temperature. 42.4 g (375 mmol) of 1-(dimethylamino)but-1-en-3-one are added dropwise to the stirred mixture at such a rate that the reaction temperature does not exceed 30 C. The mixture is subsequently stirred for a further 2 hours and hydrolyzed, and the pH of the solution is adjusted to exactly 7. The phases are separated, and the aqueous phase is extracted several times with 200 ml of ethyl acetate or methyl tert.-butyl ether, dried and subjected to fractional distillation, to give 42.0 g (75%) of 1-(4-tetrahydropyranyl)but-1-en-3-one of boiling point 93 to 95 C./5 mmHg.

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

Reference£º
Patent; BASF Aktiengesellschaft; US5221753; (1993); 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.873397-34-3,Tetrahydro-2H-pyran-3-carboxylic acid,as a common compound, the synthetic route is as follows.

873397-34-3, Step 1 : To a solution of (3-methoxy-5-methylpyrazin-2-yl)methanamine (150 mg, 979.2 u mol), tetrahydro-2H-pyran-3-carboxylic acid (127.4 mg, 979.2 Mmol) in DCM (10 mL) was added HATU (670.2 mg, 1.8 mmol) and triethylamine (198.2 mg, 1.9 mmol). The mixture was stirred at 25¡ãC for 16 hours. The mixture was diluted with water (15 mL), extracted with DCM (3 x 30 mL). The combined organic layer was washed with brine (30 mL), dried over Na2S04, filtered and concentrated. The residue was purified by preparative TLC (EA/MeOH=20/1 ) to give N-((3-methoxy-5-methylpyrazin-2-yl)methyl)tetrahydro-2H-pyran-3- carboxamide (130 mg, 50percent yield).

As the paragraph descriping shows that 873397-34-3 is playing an increasingly important role.

Reference£º
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); 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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

2-(6-(1 ,4-Diazepan-1-yl)-2-(4-fluoro-3-methoxyphenyl)-4-oxoquinazolin-3(4/-/)-yl)-lambda/- isopropylacetamide (EXAMPLE 1 i) (30 mg, 0.064 mmol), (tetrahydro-2/-/-pyran-4-yl)methyl 4-methylbenzenesulfonate (35 mg, 0.128 mmol) and DIPEA (17 mg, 21 mul, 0.128 mmol) were dissolved in DMF (1 ml_) and stirred at room temperature overnight. Purification by preparative HPLC afforded 2-{2-(4-fluoro-3-methoxyphenyl)-4-oxo-6-[4-(tetrahydropyran-4- ylmethy^perhydro-IA-diazepin-i-ylJ^H-quinazolin-S-ylj-N-isopropylacetamide (EXAMPLE 11a) (5 mg, 0.0088 mmol, 14%).Data for 2-{2-(4-fluoro-3-methoxyphenyl)-4-oxo-6-[4-(tetrahydropyran-4-ylmethyl) perhydro- 1,4-diazepin-1-yl]-4H-quinazolin-3-yl}-N-isopropylacetamide (EXAMPLE 11a): MS (ESI) m/z:, 101691-65-0

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

Reference£º
Patent; N.V. ORGANON; WO2008/33764; (2008); A2;,
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.

N-Methyl-N-(tetrahydro-2H-pyran-4-yl)amine At -70 C., 170 g (5.5 mol) of gaseous methylamine were introduced into 1.5 l of methanol. The solution was admixed dropwise with 100 g (1 mol) of sulfuric acid. 100 g (1 mol) of tetrahydro-4H-pyran-4-one and 36.4 g (0.6 mol) of sodium borocyanohydride were added in succession, and the mixture was stirred at room temperature for 3 days, resulting in a white precipitate. The solution was filtered and the filtrate was distilled. B.p. 56-58 C. (12 mm), yield 96 g. 1H NMR (270 MHz, in CDCl3): delta=1.30 (s, 1H), 1.38 (dq, 2H), 1.85 (dd, 2H), 2.43 (s, 3H), 2.57 (tt, 1H), 3.41 (dt, 2H), 3.99 (dt, 2H)., 29943-42-8

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

Reference£º
Patent; BASF Aktiengesellschaft; US6277790; (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.

Three-neck flask equipped with mechanical stirrer, thermometer, dropping funnel, 250ml of water was added to the flask, stirring was added 4-cyano-tetrahydropyran 111.14g (1mole), cooled to 0 ~ 5 C, was added at a concentration of 10 minutes 13.8% sodium hydroxide solution, a total of 290 g (1 mole), temperature controlled at 0 ~ 10 C, after each addition incubated for 15 to 20 minutes, all the alkali was added, stirred for 1 to 3 hours, the reaction was complete by gas detecting material, controlling the temperature of 0 ~ 5 C, was slowly added to a concentration of 10% sodium hypochlorite solution 1116.6g (1.5mole), plus Bi, 0 ~ 5 C for 1 hour, heated at reflux temperature for 2 hours to complete the reaction intermediate vapor detection, water cooling to 10 ~ 40 C, with 500ml dichloromethane and 50ml methanol solvent mixture and extracted 3 times, the combined extracts were recovered by distillation of methylene chloride, methylene chloride was distilled off to make, distillation to give 4-amino-tetrahydropyran 75.3 g, with a purity of 99.1%, a yield of 73.7%.

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

Reference£º
Patent; Qingdao Frontierchem Co.,Ltd; Wang, yuchen; Liu, guihong; Li, XIAOYAO; Liu, Guo Chao; (5 pag.)CN102993144; (2016); 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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A solution of [l -(6-cthyl-4,4-dimethyl-l , 2, 3,4-tetrahydro-quinolin-7-yl)-ethyl]-carbamic acid fcrt-butyl ester (17, 16 mg, 0.048 mmol), iodomethyl tetrahydropyran (72, 13 mg, 0.058 mmol), and diisopropylethylamine in 3 mL of acetonitrile was irradiated in a microwave at 180 0C for 30 minutes. The reaction mixture was concentrated under vacuum and the residue was dissolved in ethyl acetate, washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel chromatography, eluting with hexanes and ethyl acetate to provide the desired compound as a colorless oil (73, 14 mg, 68%). MS (KSl) [M+HhJ v = 431.06., 101691-94-5

The synthetic route of 101691-94-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PLEXXIKON, INC.; WU, Guoxian; IBRAHIM, Prabha N.; ZHOU, Yong; MAMO, Shumeye; GILLETTE, Samuel J.; ZHU, Yong-Liang; LIU, Jinyu; ZHANG, Chao; ZHANG, Kam; ARTIS, Dean R.; WO2010/129467; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics