Ammonium Chloride → HCID 59311442, compound

Participants

Reaction Steps

A 3 N solution of methylmagnesium bromide in diethyl ether (0.15 mL) was added dropwise to a mixture of di-tert-butyl {4-chloro-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-3-(2-oxoethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate of Step 1) of Example 3 (120 mg) and dehydrated tetrahydrofuran (1 mL) under cooling in a dry ice-acetone bath, and then the mixture was stirred for one hour. A saturated ammonium chloride solution (1 mL) was added dropwise to the reaction mixture, and then the dry ice-acetone bath was removed. The reaction mixture was separated with ethyl acetate (30 mL) and water (30 mL). Then, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (ethyl acetate-hexane) to obtain the title compound (52 mg, 42%) as an oil.

Provenance & Evidence