Hydrochloric Acid → HCID 86641323, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methanesulfonyl chloride (73 μL) in dehydrated dichloromethane was added dropwise to a mixture composed of di-tert-butyl {4-chloro-3-(2,3-dihydroxypropyl)-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate of Step 7) of Example 1 (510 mg), 2,4,6-collidine (1.15 mL) and dehydrated dichloromethane (17 mL) under cooling in an ice bath, and then the mixture was stirred for 15 hours. 0.5 N hydrochloric acid was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with water, and then dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in N,N-dimethylformamide (10 mL). Sodium bisulfide monohydrate (76 mg) was added under cooling in an ice bath, followed by stirring for 20 minutes. Potassium carbonate (142 mg) was added to the reaction mixture and the ice bath was removed. The mixture was stirred for one hour, and then heated to 50° C. and further heated with stirring for two hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and brine and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound (453 mg, 92%) as an oil.

Provenance & Evidence