Acetone → Ammonia

Participants

Reaction Conditions

Reaction Steps

A solution of {4-[5-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-[1,2,4]triazolo[4,3-c]pyrimidin-7-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine (0.25 g, 0.61 mmol) in chloroform (5 mL) were added acetone (1 mL) and sodium triacetoxyborohydride (0.45 g, 2.14 mmol) and stirred at 70° C. for 2 h. Upon cooling to room temperature, the reaction was diluted with methylene chloride and washed with saturated sodium bicarbonate, brine, and dried (K2CO3). Flash chromatography of the crude product with 1% 2M NH3 in MeOH/CHCl3 afforded the title compound as an off-white solid. MS (ES+): 455.2 [M+H]+, 453.2 [M−H]−.

Provenance & Evidence