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

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Reaction Steps

2-(3-Methoxy-4-(6-methylpyridazin-4-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine-4-carbaldehyde (100 mg, 0.23 mmol) was dissolved in DCE (4 mL), THF (1 mL) and DMF (0.1 mL). Benzylamine (0.030 mL, 0.28 mmol) and acetic acid (0.013 mL, 0.23 mmol) were added followed by sodium triacetoxyborohydride (69 mg, 0.32 mmol). The mixture was stirred at rt under nitrogen atmosphere for 1 hour. The reaction was quenched with water. The water phase was extracted by DCM (×2). The combined organic layer was dried over anhydrous sodium sulfate and evaporated onto silica. The silica was loaded on a pre-packed silica column. The column was eluted with a gradient of methanol in DCM to give the title compound as a solid, 58 mg (48%).

Provenance & Evidence