Category: 101691-94-5

Simple exploration of 101691-94-5

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

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

Preparation 8: Triphenyl(tetrahydropyran4-ylmethyl)phosphonium iodide; PPh,iA mixture of Preparation 7 (350g5 1.55M) and triphenylphosphine (406g, 1.55M) in acetonitrile (1.6L) was heated under reflux. After 27h the mixture was cooled and filtered, washed with diethyl ether and dried in air to provide a white solid (504g). Filtrate and washings were returned to reflux and concentrated to 750mL, reflux was maintained for 16h before cooling and dilution with diethyl ether (ca 1,2L). A precipitate formed which was stirred for 30min before being filtered, washed with diethyl ether (2 x 300mL) and dried in air to yield a further crop (lOOg). Overall yield of the title compound (604 g, 80%). RT = 2.7min; m/z (ES+) = 361.2.

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; PROSIDION LIMITED; WO2006/16178; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 101691-94-5

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

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;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 101691-94-5

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

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.

Step 2: Methyl 2-cyclopropyl-6-((tetrahydro-2H-pyran-4-yl)methoxy)isonicotinate To a stirring suspension of methyl 6-cyclopropyl-2-oxo-l,2-dihydropyridine-4-carboxylate (212 mg, 1.1 mmol) in acetonitrile (5 mL) were added potassium carbonate (455 mg, 3.29 mmol) and 4-(iodomethyl)tetrahydro-2H-pyran (CAS-RN 101691-94-5; 744 mg, 3.29 mmol). The reaction mixture was heated at 80C for 16 h and then evaporated in vacuo. The residue was purified by chromatography (silica gel; heptane-ethyl acetate gradient) to produce the title compound (188 mg, 59%). Colourless oil, MS: 292.2 (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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DI GIORGIO, Patrick; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; MATTEI, Patrizio; RUDOLPH, Markus; WO2015/144605; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Analyzing the synthesis route of 101691-94-5

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

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.

101691-94-5, Reference Example 3 methyl 2-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoate [Show Image] To a solution of diisopropylamine (4.0 mL) in tetrahydrofuran (60 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 methyl [1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]acetate (4.68 g) in tetrahydrofuran (5 mL) was slowly added thereto. The reaction mixture was stirred at – 70C for 15 min, and 4-(iodomethyl)tetrahydro-2H-pyran (5.80 g) was added thereto. 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 (2.57 g, yield 37%) as a pale-yellow oil from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS:299(MH+).

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

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2266983; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 101691-94-5

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

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.

Step 3 [0341] 4-(Iodomethyl)tetrahydro-2H-pyran obtained in Step 2 (0.940 g, 4.16 mmol) was dissolved in acetonitrile (10 mL), triphenylphosphine (1.09 g, 4.16 mmol) was added thereto, and the mixture was stirred for 13 hours under reflux with heating. The solvent in the reaction mixture was evaporated under reduced pressure, diethyl ether was added to the residue, and the precipitated crystal was collected by filtration, whereby triphenyl[(tetrahydro-2H-pyran-4-yl)methyl]phosphonium iodide (0.600 g, 30%) was obtained. 1H NMR (300 MHz, DMSO-d6, delta): 7.90-7.74 (m, 15H), 3.68-3.61 (m, 4H), 3.16-3.13 (m, 2H), 2.02-1.91 (m, 1H), 1.41-1.31 (m, 4H)., 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; Kyowa Hakko Kirin Co., Ltd.; FURUTA, Takayuki; SAWADA, Takashi; DANJO, Tomohiro; NAKAJIMA, Takahiro; UESAKA, Noriaki; EP2881394; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 101691-94-5

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

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.

2 g (10.3 mmol) 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2.9 mL (20.6 mmol) 4-(iodomethyl)-tetrahydro-2H-pyran are dissolved in 200 mL DMF and 4.274 g (30.9 mmol) K2CO3 are added. The mixture is shaken at 80 C. for 5 h. After cooling to r.t. the mixture is filtered, the filtrate is concentrated in vacuo to approximately 60 mL. The product is separated using HPLC-MS (Gilson, mass flow 120 mL/min, 10 mum, 200 g Sunfire RP18, ACN/water/TFA). The product fractions are combined and freeze-dried to yield 115 mg product (3.8%) R6.3

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 101691-94-5

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

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,101691-94-5

A solution of 4-(iodomethyl)tetrahydro-2H-pyran ([101691-94-5], 565 mg, 3 mmol) in LiC1 solution (0.5 M in THF, 5 mL, 3 mmol) was pumped using the R2 + R4 through a column containing activated Zn (12 g) at 0.5 mL/min at 60 C. Titration with 12/LiC1 showed a concentration of organozinc reagent of 0.28 M. The solution was used in the next step without further purification.

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

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; VOS, Ann, Marleen; OEHLRICH, Daniel; GIJSEN, Henricus, Jacobus, Maria; WATTS, Karl, Shawn; BHAT, Sathesh, Pangala; BUIJNSTERS, Peter, Jacobus, Johannes, Antonius; VAN BRANDT, Sven, Franciscus, Anna; ALCAZAR-VACA, Manuel, Jesus; (57 pag.)WO2018/162444; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 101691-94-5

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

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-(2,6-dichlorophenyl)-1 -[(1 S)-4-iodo-1-methyl-1 ,3-dihydro-2H-isoindol-2-yl]ethanone a48(100 mg, 0.22 mmol), sodium metabisulfite (87 mg, 0.45 mmol), tetrabutylammonium bromide (80 mg, 0.25 mmol), sodium formate (34 mg, 0.49 mmol), palladium(Il) acetate (5mg, 0.02 mmol), 1,10-phenanthroline (12 mg, 0.07 mmol) and triphenylphosphine (18 mg, 0.07 mmol) were mixed in DMSO (2 mL). The mixture was stirred at 70 C for 2 h. The reaction mixture was cooled to rt, then 4-(iodomethyl)tetrahydro-2H-pyran (100 mg, 0.44mmol) was added. The mixture was stirred at ft for 16 h, then diluted with DCM (50 mL) and successively washed with water (50 mL) and brine (50 mL). The organic layer was dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by reverse phase chromatography (basic mode, LCMS prep) to yield 12 mg of 2-(2,6- dichlorophenyl)-1 -{(1 S)-1 -methyl-4-[(tetrahydro-2H-pyran-4-ylmethyl)sulfonyl]- 1 ,3-dihydro-2H-isoindol-2-yl}ethanone 42 as a white solid.Yield: 10%.LCMS (ES) 482/484/486 (M-?-H), 96.78 % purity.

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

Reference£º
Patent; UCB BIOPHARMA SPRL; SKOLC, David; ATES, Ali; JNOFF, Eric; VALADE, Anne; (99 pag.)WO2016/55482; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 101691-94-5

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

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.

To a solution of diisopropylamine (2.19 ml. 15.36 mmol) in TetaF (20 mL) at-78 C, was added ?-butyl lithium ( 6.46 ml, 2.5M in hexane, 16.15 mmol) dropwise. The resulting mixture was stirred at -78 C for 30 min and was then added to a mixture of 1 ,1 -dimethylethyl {2-[[(l/?,2/?)-2-hydroxy-l-methyl-2- phenylethyl](methyl)amino]-2-oxoethyl}methylcarbamate (2.65 g ,7.88 mmol) and lithium chloride (2.Og, 47.3 mmol) via cannula at -23 C. The resulting mixture was stirred for 24 h and allowed to warm to room temperature before it was recooled in an ice bath and quenched with HCl (IM, 15.8 ml ). The mixture was then extracted with EtOAc (3 x 20 ml) and the combined extracts washed with saturated NH Cl, brine, dried, filtered, and concentrated. This crude product was purified by column chromatography (16O g silica gel 60, 230-400 mesh, 25,30,40, then 50% EtOAc/hexanes) to provide 1,1 -dimethylethyl [(15)-2-[[(l/?,2/?)-2-hydroxy-l- methyl-2-phenylethyl](methyl)amino]-2-oxo-l-(tetrahydro-2H-pyran-4- ylmethyl)ethyl]methylcarbamate (510 mg, 95% pure and 1.2 g, 80% pure, 42% combined yield). MS (m/z) 435.2 (M+eta+).

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

Reference£º
Patent; VITAE PHARMACEUTICALS, INC.; WO2008/156817; (2008); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Analyzing the synthesis route of 101691-94-5

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

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.

Under argon, 1.31 ml of 1,1,1,3,3,3-hexamethyldisilazane are dissolved in 20 ml of tetrahydrofuran. With ice cooling, 2.3 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 tert-butyl 2-ethoxycarbonylmethyl-5,5-dioxo-5H-phenothiazine-10-carboxylate in 100 ml of tetrahydrofuran. The reaction mixture is stirred at -78 C. for 20 minutes, and 1.1 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 (50%:50%). This gives 700 mg of tert-butyl 2-[1-ethoxycarbonyl-2-(tetrahydropyran-4-yl)ethyl]-5,5-dioxo-5H-phenothiazine-10-carboxylate. C27H33NO7S (515.63), LCMS (ESI): 533.2 (M+NH4+), 460.1 (M-tert-butyl+H+), Rf (n-heptane:EA=1:1)=0.28.

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

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