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 2- (4-methoxymethylsulfanylphenyl)-3- (tetrahydropyran-4-yl)-N thiazol-2-ylpropionamide (EXAMPLE 77,1. 29g, 3. 28MMOL) in THF (50ML) was added to a stirred solution OF AGN03 (0.59g, 3. 28MMOL) in ETOH (85mL) at 40 C. The mixture was protected from light and stirred at 40 C for 21h. The solvents were evaporated off under reduced pressure, then the remaining solid was triturated with i-PrOH (60mL), THF (60mL), and ET20 (60mL). After air-drying, the solid was stirred vigorously with CH2C12 (200mL) and 6M HCl (82mL) for 4h under Ar. The layers were separated, then the aqueous phase was extracted with CH2Cl2 (2 x 100ML). The combined organic extracts were filtered through Celite, washed with brine (LOOML) and dried (MGS04). Filtration and solvent evaporation furnished 2- (4- MERCAPTOPHENYL)-3- (TETRAHYDROPYRAN-4-YL)-N-THIAZOL-2-YLPROPIONAMIDE : m/z (ES+) = 349.2 [M + H] +. NEt3 (0.14mL, 1006mumol) and a solution of 4- iodomethyltetrahydropyran (151 mg, 668MOL) in anhydrous DMF (3mL) were added to a stirred solution of this benzenethiol (197mg, 565, UMOL) in anhydrous DMF (7mL) at 0 C. The mixture was warmed to 20 C, before being stirred for 16h. The solvents were evaporated off under reduced pressure, then the residue was partitioned between CH2C12 (25ML) and 2% aqueous citric acid (lOmL). The aqueous layer was extracted with CH2C12 (10mL), then the combined organic layers were washed with H20 (LOML), saturated aqueous NA2C03 (LOML), H20 (LOML), and brine (LOML). After drying (MGS04), filtration and solvent evaporation gave a residue that was subjected to flash chromatography (1H ETOAC, 3: 1 to 0: 1) to furnish the title compound: RTA= 3. 61MIN ; MLZ (ES+) = 447.3 [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; OSI PHARMACEUTICALS, INC.; WO2004/72031; (2004); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics