Boron tribromide → HCID 19597403, compound

Participants

Reaction Conditions

Reaction Steps

A solution of boron tribromide in dichloromethane (0.9 ml of a 1M solution) was added dropwise with stirring to a solution of the product from Example 32, N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzamide (130 mg) in dichloromethane (6 ml) at -10° C. under nitrogen, after the addition the reaction mixture was allowed to warm to 0° C. and stirred at 0° C. for 1.5 hours. The reaction mixture was quenched by the dropwise addition of saturated aqueous sodium bicarbonate solution (5 ml) at 0° C. There was an exotherm and the temperature of the mixture rose to 10° C. The mixture was allowed to warm to ambient temperature, then extracted with dichloromethane to give N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-hydroxyphenyl]benzamide, m.p. 173-175° C. (with decomposition). The structure was confirmed by 1H nmr and mass spectra.

Provenance & Evidence