Phenol → HCID 57964899, compound

Participants

Reaction Steps

Sodium hydride [60% dispersion in paraffin; 1.5 equivalents] in DMF was added to a solution of phenol (1 equivalent) in dimethylformamide (0.2 M) at 0° C. under nitrogen. After 30 minutes, 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 1 equivalent) was added and the mixture was stirred for 12 h at room temperature. Saturated aqueous ammonium chloride was added and the solution was extracted with ethyl acetate. The combined organic extracts were dried (sodium sulfate), filtered, evaporated, and purified by chromatography on neutral alumina, eluting with ethyl acetate/hexane, to give 4-(4-phenoxy-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence