Potassium Carbonate → HCID 24811286, compound

Participants

Reaction Steps

Sodium bisulfide monohydrate (3.8 mg) was added to a mixture of the above 2-{6-[bis(tert-butoxycarbonyl)amino]-4-chloro-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methylethyl 4-methylbenzenesulfonate (29 mg) and N,N-dimethylformamide (1 mL) under cooling in an ice bath, and the mixture was stirred for 20 minutes. Then, potassium carbonate (8.2 mg) was added and the ice bath was removed, followed by stirring for 10 hours. The reaction mixture was diluted with ethyl acetate and then sequentially washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane (2 mL). Then, trifluoroacetic acid (0.5 mL) was added and the mixture was stirred for two hours. The reaction mixture was concentrated under reduced pressure. Then, the resulting residue was dissolved in chloroform and sequentially washed with a saturated sodium bicarbonate solution and water. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol) to obtain the title compound (8.9 mg, 63%) as a solid.

Provenance & Evidence