Category: Tetrahydropyrans

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.

In a 500mL reaction flask, add intermediate V4 (24.5g, 32mmol, 1.0eq), intermediate VM4 (13g, 41mmol, 1.3eq) and 800mL dichloromethane, stir to dissolve, then add CDI (7.7g, 48mmol, 1.5eq ) And 2.5g DMAP, heated to 30-35 reaction,TLC monitors the reaction.After the reaction is completed, add 300mL of 10% acetic acid aqueous solution and stir for 30min to separate the organic phase.The organic phase was washed with saturated aqueous sodium bicarbonate solution (200 mL ¡Á 1) and saturated aqueous sodium chloride solution (200 mL ¡Á 1), dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was concentrated under reduced pressure to obtain a crude solid product. The crude product was recrystallized with 300 mL of ethyl acetate and n-hexane (1: 1),29.2 g of solid product V5 was obtained.Yield: 87%.

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

Reference£º
Patent; Nantong Changyou Pharmaceutical Technology Co., Ltd.; Li Zebiao; Chen Dan; Wu Hongdang; Xu Xiaohong; Lin Yanfeng; (9 pag.)CN110878098; (2020); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: In air, CuBr (7.1 mg, 0.05 mmol), PPh3 (17.03 mg, 0.065 mmol), LiOtBu(80 mg, 1mmol), and bis(neopentyl glycolato) diboron (168mg, 0.75 mmol ) were added to aSchlenk tube equipped with a stir bar. The vessel was evacuated and filled with argon(three cycles). DMAc (1 mL), alkyl halide (0.5 mmol) were added in turn by syringeunder an argon atmosphere (if the alkyl halide is a solid, it was added along with theCuBr). The resulting reaction mixture was stirred vigorously at 25 C for 18 h. Thereaction mixture was then diluted with EtOAc, filtered through silica gel with copiouswashings (petroleum ether to EtOAc), concentrated, and purified by columnchromatography., 25637-16-5

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

Reference£º
Article; Lou, Xin; Zhang, Zhen-Qi; Liu, Jing-Hui; Lu, Xiao-Yu; Chemistry Letters; vol. 45; 2; (2016); p. 200 – 202;,
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.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Tetraethyl 4-(2-Tetrahydro-2H-pyranyloxy)butylene-1,1-bisphosphonate (34). To a suspension of NaH (60% suspension in mineral oil, 900 mg, 22.0 mmol) in dry THF (20 mL) was added dropwise tetraethyl methylenebisphosphonate (6.46 g, 22.4 mmol). The resulting clear solution was stirred 15 min at room temperature, after which 2-(3-bromopropoxy)tetrahydro-2H-pyran (5.05 g, 22.6 mmol) was added dropwise. The reaction mixture was heated to reflux for 6 h, diluted with CH2Cl2 (75 mL) and washed with brine (2*50 mL), dried (MgSO4) and evaporated. It was used as such in the following step., 33821-94-2

The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TARGANTA THERAPEUTICS, INC.; US2010/113333; (2010); 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.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

c) To a solution of 425 mg (2.5 mmol) of ethyl 2-(tetrahydro-2H-pyran-4- yl)acetate in 10 mL of dry THF cooled at 05C under argon, a 2.71 mL of a solution of LiAII-U 1 M in THF was added. Bubbling was observed. It was stirred at room temperature for 30 min. Then it was quenched with wet EtAcO, dried with MgS04 and filtered through celite, washing with abundant EtAcO. After removing the solvent the desired compound, 2-(tetrahydro-2H-pyran-4-yl)ethanol, was obtained (300 mg, 93%).

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; DRACONIS PHARMA, S.L.; ALMIRALL, S.A.; TORRENS JOVER, Andoni; MERCE VIDAL, Ramon; CALDENTEY FRONTERA, Francesc Xavier; RODRIGUEZ GARRIDO, Antonio, David; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/37960; (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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

Synthesis of methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)-5-fluoropicolinate A mixture of methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinate (1.0 equiv.), 4-(bromomethyl)tetrahydro-2H-pyran (2.0 equiv.) and K2CO3 (4.0 equiv.) in DMF (0.20 M) was heated at 100 C. for 20 min in microwave. The reaction mixture was cooled off to rt and partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)-5-fluoropicolinate in 100% yield. LC/MS=382.0 (MH+), Rt=0.97 min., 125552-89-8

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

Reference£º
Patent; Burger, Matthew; Ding, Yu; Han, Wooseok; Nishiguchi, Gisele; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225061; (2012); A1;; ; Patent; Burger, Matthew; Nishiguchi, Gisele; Machajewski, Timothy D.; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225062; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.85064-61-5,Tetrahydropyranyl-4-acetic acid,as a common compound, the synthetic route is as follows.

A solution of sodium hydroxide (15.9 g, 44.06 mmol) in water (150 ml) was added dropwise to a solution of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (15 g, 8.81 mmol) in methanol (150 ml) at a temperature of 0 ¡ãC or below, and the mixture was stirred at room temperature for 15 hr. The solvent of the reaction mixture was removed by distillation under reduced pressure, and the water layer was adjusted to pH 3 by the addition of 1 M hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure to give a corresponding acid as a colorless solid (12.0 g, 94percent). This compound was used in the next step without further purification. Benzyl bromide (14.3 g, 83.33 mmol) was added dropwise to a suspension of this compound (10.0 g, 69.44 mmol) and anhydrous potassium carbonate (28.8 g, 208.3 mmol) in acetonitrile (100 ml) at room temperature, and the mixture was refluxed for 48 hr. The solvent of the mixture was removed by distillation under reduced pressure, the residue was diluted with water and was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate = 9:1) to give the tile compound as an oil (12.0 g, yield 75percent). 1H-NMR (400 MHz, CDCl3): delta (ppm) 7.39-7.34 (m, 5H), 5.12 (s, 2H), 3.95-3.92 (m, 2H), 3.42-3.36 (m, 2H), 2.30 (d, J = 7.2 Hz, 2H), 2.09-1.99 (m, 1H) 1.64-1.61 (m, 2H), 1.39-1.29 (m, 2H); MS (ESI): m/z 234 (M+).

The synthetic route of 85064-61-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Meiji Seika Pharma Co., Ltd.; MORINAKA, Akihiro; MAEBASHI, Kazunori; IDA, Takashi; HIKIDA, Muneo; YAMADA, Mototsugu; ABE, Takao; EP2737900; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a cooled solution of 79 (0.5 g, 1.17 mmol, 1.0eq), and 79.1 (0.386 g, 2.34 mmol, 1.2 eq) inAcetonitrile (15mE) at 0 C. was added Cesium carbonate (0.9 g, 2.92mmol, 2.5 eq). The reaction was stirred at 70 C. for 2 h. Afier completion of reaction, reaction mixture was transferred into water and product was extracted with ethyl acetate. Organic layer was combined and dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography and compound was eluted in 20% ethyl acetate in hexane to obtain pure 79.2. (0.150 g, 25.06%). MS (ES):mlz 511.24 [M+H]., 25637-16-5

25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Nimbus Lakshmi, Inc.; Masse, Craig E.; Greenwood, Jeremy Robert; Mondal, Sayan; Cowen, Scott D.; McLean, Thomas H.; (624 pag.)US2019/31664; (2019); 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.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

Under nitrogen atmosphere, magnesium (6.05 g, 249 mmol) was suspended in THF (30 ml). A catalytic amount of iodine and dibromoethane (0.4 ml) were added. The mixture was heated to 60C and 4-chlorotetrahydro-2H-pyran (5 g, 41.5 mmol) in THF (5 ml) was added dropwise. The mixture was stirred at 60C for 2.5 h. The mixture was cooled to 0C and N-[[5-benzyloxy-l-[2- [tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-2-pyridyl]methylene]-2-methyl-propane-2- sulfinamide (Intermediate 5, 6.78 g, 13.82 mmol) in THF (20 ml) was added. The resulting mixture was stirred at rt for 45 min. The reaction was quenched with ammonium chloride solution and extracted with EtOAc (2x). The combined organic layers were washed with brine, dried with sodium sulfate and concentrated to afford the title intermediate as an orange gum (8.7 g). Purification by chromatography (Si02, 10% MeOH in DCM) gave the title intermediate as an orange oil (7.3 g, 56 %). MS, ES+ m/z, 577 (M+H)+.

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

Reference£º
Patent; LIEBER INSTITUTE FOR BRAIN DEVELOPMENT; BARROW, James; ERNST, Glen; SWINNEN, Dominique; MONTEL, Florian; DEFAYS, Sabine; (224 pag.)WO2017/91818; (2017); 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.

Example 4 N-(4-Ethoxy-6-{4-oxo-2-[(tetrahydro-pyran-4-ylmethyl-amino)-4H-thiazol-5-ylidenemethyl}-quinolin-2-yl]-acetamide 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).

29943-42-8, 29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

A suspension solution of152F (30 mg, 0.089 mmol), 4-(bromomethyl)tetrahydropyran (16.73 mg, 0.093 mmol)and C52CO3 (43.5 mg, 0.133 mmol) in DMF (1 mL) was heated to 120 C for 20 mm and 140 C for 1 h under microwave conditions. The reaction mixture was concentrated invacuo. Water (2 mL) was added and stirred for 5 minutes. The solid was collected as the crude product which was purified by column chromatography on the Isco system to yield152G (25 mg, 65% yield). MS(ESI) m/z 435.2 (M+H)., 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HART, Amy C.; PITTS, William J.; MASTALERZ, Harold; GUO, Junqing; BROWN, Gregory D.; (148 pag.)WO2016/100166; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics