Category: 101691-94-5

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

Reference Example 16 ethyl 2-(4-bromo-5-methoxy-1H-indazol-1-yl)-3-(tetrahydro-2H-pyran-4H-yl)propanoate [Show Image] To a solution of diisopropylamine (1.35 g) in a mixed solvent of tetrahydrofuran (30 mL) and 1,3-dimethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one (15 mL) was slowly added 1.6M hexane solution (16.1 mL) of n-butyllithium at -70C under a nitrogen atmosphere. The reaction mixture was stirred at -70C for 15 min, and a solution of ethyl (4-bromo-5-methoxy-1H-indazol-1-yl)acetate (3.65 g) in tetrahydrofuran (5 mL) was slowly added thereto. The reaction mixture was stirred at – 70C for 20 min, 4-(iodomethyl)tetrahydro-2H-pyran (2.80 g) was added thereto, and the mixture was stirred overnight at room temperature. To the reaction mixture was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (1.36 g, yield 28%) as pale-yellow crystals from the fraction eluted with ethyl acetate-hexane (2:3, volume ratio). melting point 76-77C. MS:413(MH+)., 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; Takeda Pharmaceutical Company Limited; EP2266983; (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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of (6a/?,9a5)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-cyclopent[4,5]imidazo[l,2-alpha]pyrazolo[4,3-e]pyrimidin-4(2H)-one (50 mg, 0.155 mmol), 4-(iodomethyl)-tetrahydro-2H-pyran (70 mg, 0.310 mmol), and Cs2CO3 (101 mg, 0.310 mmol) in DMF (1 mL) is heated in microwave at 140 0C for 30 min. After cooling, the mixture is filtered through a 0.45 mum microflter, and the filtrate is purified by a semi-preparative HPLC to give pure product as white powder. MS (ESI) m/z 421.2 [M+H]+., 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; INTRA-CELLULAR THERAPIES, INC.; WO2009/75784; (2009); 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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Synthesis of 3-Methoxy-4-(tetrahydro-pyran-4-ylmethoxy)-benzonitrile (For Example1 .0 g 4-Hydroxy-3-methoxybenzonitrile, 1.1 g potassium carbonate and 2.0 g 4-(iodomethyl)- tetrahydropyran were placed in 20 mL acetone and heated to reflux overnight. After this time,1 .1 g potassium carbonate was added and the reaction was heated at reflux for a further 2 h before more 0.93 g potassium carbonate was introduced and reflux was continued for a further 3 h. The mixture was then cooled to ambient temperature and concentrated under reduced pressure. The material that remained was partitioned between diethyl ether and water and the aqueous phase was removed and extracted with additional diethyl ether. The combined organic fractions were dried, filtered and the filtrate was concentrated under reduced pressure. Purification by silica gel chromatography (Si02: ethyl acetate/heptanes: 10% to 30%) provided the title compound. Yield: 307 mg (19% of theory)Analysis: HPLC-MS (Method B): Rt: 1 .85 min., 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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; DAHMANN, Georg; FIEGEN, Dennis; HANDSCHUH, Sandra; KLICIC, Jasna; LINZ, Guenter; SCHAENZLE, Gerhard; SCHNAPP, Andreas; EAST, Stephen P.; MAZANETZ, Michael Philip; SCOTT, John; WALKER, Edward; WO2011/92128; (2011); 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 1-bromo-4-(ethylsulfonyl)benzene (1.50 g) in 1,4-dioxane (20 mL) were added diethyl malonate (1.16 g), potassium phosphate (3.84 g), biphenyl-2-yl(di-tert-butyl)phosphine (108 mg) and palladium acetate (II) (40 mg). The reaction solution was purged with argon, and the mixture was heated under reflux for 12 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane = 10:90 – 50:50, volume ratio) to give a colorless oil. A solution of the obtained oil in N,N-dimethylformamide (20 mL) was purged with nitrogen, sodium hydride (60%, oil, 213 mg) was added under ice-cooling, and the mixture was stirred at 0C for 15 min. To the reaction solution was added a solution of 4-(iodomethyl)tetrahydro-2H-pyran (1.15 g) in N,N-dimethylformamide (10 mL) at 0C, and the mixture was stirred for 3 hr at 90C. The reaction mixture was concentrated under reduced pressure, saturated aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane = 10:90 – 40:60, volume ratio) to give a colorless oil. To a solution of the obtained oil in a mixed solvent of tetrahydrofuran (40 mL) and methanol (20 mL) was added 2M aqueous sodium hydroxide solution (10 mL), and the mixture was stirred at 60C for 3 hr. The reaction solution was cooled to room temperature, and acidified with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give the title compound (1.33 g, yield 67%) as colorless crystals. MS:327(MH+). Reference Example 67 4-[4-(ethylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one, 101691-94-5

As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2149550; (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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A solution of N,N-diisopropylamine (3.65 mL) in tetrahydrofuran (50 mL) was purged with nitrogen, a 1.6M n-butyllithium hexane solution (16.1 mL) was added at -78C, and the mixture was stirred at -78C for 30 min. To the reaction solution was added dropwise a solution of ethyl [6-(methylsulfanyl)pyridin-3-yl]acetate (4.55 g) in tetrahydrofuran (40 mL), and the mixture was stirred at -78C for 30 min. To the reaction solution was added a solution of 4-(iodomethyl)tetrahydro-2H-pyran (5.83 mL) in tetrahydrofuran (40 mL), and the mixture was stirred at -78C for 2 hr. The reaction solution was warmed to room temperature, and stirred at room temperature for 3 days. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane = 10:90 – 50:50, volume ratio) to give the title compound (3.90 g, yield 59%) as a pale-yellow oil. MS:310(MH+). _, 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; Takeda Pharmaceutical Company Limited; EP2149550; (2010); 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

In a round bottom flask under argon was placed tetrahydrofuran (30 mL) and 1,1,1,3,3,3-hexamethyldisilazane (1.50 mL, 7.13 mmol) and it was cooled to -78 C. in a dry ice/acetone bath. To this cooled solution was then added n-butyl lithium (2.5 M solution in hexanes, 2.70 mL, 6.69 mmol) and it was stirred for 15 min at -78 C. To this cooled solution was then added a solution of (3-methyl-4-methylsulfanyl-phenyl)-acetic acid methyl ester (1.34 g, 6.37 mmol) in tetrahydrofuran (20 mL) dropwise. This was then stirred for 10 min at -78 C. then at 0 C. for 1 h which resulted in an gold colored solution. After such time, the reaction was cooled back to -78 C. and a solution of 4-iodomethyl-tetrahydro-pyran (prepared as in PCT WO 2003/095438 A1, Example 20, 1.73 g, 7.64 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1.17 mL, 9.56 mmol) was added dropwise at -78 C. The reaction was then allowed to slowly warm to 0 C. and it was stirred for 16 h. After such time, the reaction was diluted with ethyl acetate (250 mL) and washed with a saturated aqueous ammonium chloride solution (1¡Á50 mL) followed by a saturated sodium chloride solution wash (1¡Á50 mL). The organics were dried over sodium sulfate, filtered and then concentrated with silica gel (4 g) in vacuo and purified on Biotage Flash chromatography system (40M column, silica gel, 10% ethyl acetate/hexanes) to afford 2-(3-methyl-4-methylsulfanyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (1.49 g, 76%) as a gold oil., 101691-94-5

As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; Berthel, Steven Joseph; Kester, Robert Francis; Murphy, Douglas Eric; Prins, Thomas Jay; Ruebsam, Frank; Sarabu, Ramakanth; Tran, Chinh Viet; Vourloumis, Dionisios; US2008/21032; (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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of intermediate XIX.1 (500 mg; 1.21 mmol) and 4-iodomethyl-tetrahydropyrane (1.07 g; 4.73 mmol) in ACN (5.0 ml) is heated to 120 C. (microwave heating; closed vessel) for 7 h. Additional 4-iodomethyl-tetrahydropyran (1.07 g; 4.73 mmol) is added and the mixture is again heated to 120 C. (microwave heating; closed vessel) over night. Volatiles are evaporated and the crude product is purified by RP-HPLC (modifier: TFA) to yield the title compound. [0212] C25H40ClN4O5¡ÁC2F3O2 ESI Mass spectrum: m/z=511 [M]+, 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; Boehringer Ingelheim International GmbH; KLEY, Joerg; FRATTINI, Sara; HAMPRECHT, Dieter; US2015/18315; (2015); 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

2 g (1 0.3 mmol) 4-( 4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole and 2.9 mL (20.6mmol) 4-(iodomethyl)-tetrahydro-2H-pyran are dissolved in 200 mL DMF and 4.274 g (30.9s mmol) K2C0 3 are added. The mixture is shaken at 80″C for 5 h. After cooling to r.t. the mixture isfiltered, the filtrate is concentrated in vacuo to approximately 60 mL. The product is separatedusing HPLC-MS (Gilson, mass flow 120 mL/min, 10 lJ.m, 200g Sunfire RP18, ACN/waterfTFA).The product fractions arc combined and frecze-d1icd to yield 115 mg product (3.8 %) R6.3., 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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140081; (2014); 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.101691-94-5,4-(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

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

Under argon, 1.66 ml of 1,1,1,3,3,3-hexamethyldisilazane are dissolved in 20 ml of tetrahydrofuran. With ice cooling, 2.90 ml of n-butyllithium (2.5 M in n-hexane) are added dropwise, and the mixture is stirred at 0 C. for another 30 minutes. At -78 C., this solution is then added dropwise to a stirred solution of 2.0 g of ethyl (10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)acetate in 100 ml of tetrahydrofuran. The reaction mixture is stirred at -78 C. for 20 minutes, and 2.0 g of 4-(iodomethyl)tetrahydro-2H-pyran are then added dropwise. The cooling bath is removed and the mixture is allowed to slowly warm to room temperature. The reaction mixture is stirred at room temperature overnight. 10 ml of water are then added, the tetrahydrofuran is removed under reduced pressure and the residue is extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases are dried over MgSO4 and then concentrated under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate (100%:0%)=>n-heptane:ethyl acetate (0%:100%). This gives 2.0 g of ethyl 2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionate as a colorless solid. C23H27NO5S (429.54), LCMS (ESI): 430.2 (M+H+).

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; SANOFI-AVENTIS; US2009/325942; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics