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

Participants

Reaction Steps

3-Fluoroazetidine hydrochloride (31 mg, 0.28 mmol) was mixed with methanol (5 mL). Sodium methoxide (0.051 mL, 0.28 mmol) was added followed by 2-(3-methoxy-4-(6-methylpyridazin-4-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde (100 mg, 0.23 mmol). The mixture was stirred for 2 min. Acetic acid (0.042 mL, 0.74 mmol) was added. The mixture was stirred for 5 min. Sodium cyanoborohydride (20 mg, 0.32 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 solid, 48 mg (42%).

Provenance & Evidence