To a mixture of 2,2,2-trifluoro-N-(3-oxo-1-{4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-2) (20 mg, 0.035 mmol) and dimethylamine (2M in THF, 0.052 mL, 0.104 mmol) in MeOH (0.3 mL) was added Zn(BH3CN)2 (0.3M in MeOH, 0.6 mL, 0.18 mmol), and the mixture was stirred at room temperature for overnight. To the mixture was added EtOAc, sat. NaHCO3, and brine. The resulting solid was collected by filtration to give N-(3-(dimethylamino)-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)-2,2,2-trifluoroacetamide (4-4) as colorless solid. HRMS (M+H)+: observed=609.2338, calculated=609.2342.
