Dichloromethane → HCID 178463544, compound

Participants

Reaction Steps

To a cooled solution of N-(1-{8-chloro-5-[(3S)-3-methoxypyrrolidin-1-yl]imidazo[1,5-a]pyridin-6-yl}ethyl)-9H-purin-6-amine (18.0 mg, 0.0436 mmol) in methylene chloride (1.0 mL, 16 mmol) at −78° C. under an atmosphere of nitrogen was added slowly 1.0 M boron tribromide in methylene chloride (0.47 mL, 0.47 mmol). The mixture was allowed to warm up to room temperature and stirred for 30 minutes. The resultant mixture was quenched with Na2CO3 (aq). The cloudy suspension was filtered and washed with water. The filtrate was extracted with ethyl acetate and the organic layer was washed with brine and evaporated. Purification by preparative LCMS (pH 10) gave the desired compound (2.0 mg, 12%). LCMS calculated for C18H20ClN8O (M+H)+: m/z=399.1. found: 399.0.

Provenance & Evidence