Acetic Acid → 4-((3-Fluoroazetidin-1-yl)methyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-2-amine

Participants

Reaction Steps

3-Fluoroazetidine hydrochloride (25 mg, 0.23 mmol) was mixed with methanol (5 mL). Sodium methoxide (30 w % in methanol, 0.042 mL, 0.23 mmol) was added followed by 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde (80 mg, 0.19 mmol). The mixture was stirred for 2 min. Acetic acid (0.035 mL, 0.61 mmol) was added and the mixture was stirred for 5 min. Sodium cyanoborohydride (17 mg, 0.27 mmol) was added and the mixture was stirred at rt under nitrogen atmosphere for 1 h. Water was added and the mixture was stirred for 5 min. The solvents were evaporated and the residue was purified by preparative HPLC to give the title compound as a dry film 44 mg (48%).

Provenance & Evidence