Potassium Permanganate → Ethyl 2-(3-methoxy-4-(6-methylpyridazin-4-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidine-4-carboxylate

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Reaction Steps

4-(1-Ethoxyvinyl)-N-(3-methoxy-4-(6-methylpyridazin-4-yl)phenyl)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-2-amine (0.7 g, 1.47 mmol) was dissolved in 1,4-dioxane (50 mL). Sodium metaperiodate (0.630 g, 2.94 mmol) was suspended in water (25 mL) and sonicated until a clear solution was obtained then added to the dioxane-solution. Potassium permanganate (0.035 g, 0.22 mmol) was added and the mixture was stirred at rt. Additional 10-15 mg of potassium permangante was added every 10 min. After 45 min the reaction mixture was filtered and the filter was washed with EtOAc. To the filtrate were sodium bicarbonate (s) and sodium chloride (s) added and the mixture was stirred for 5 min. The phases were separated and aqueous layer was extracted with ethyl acetate (×2). The combined organic layer was dried over sodium sulfate, filtrated and evaporated. The residue was purified by column chromatography on silica eluting with a gradient of methanol in DCM to give the title compound as a solid, 595 mg (85%).

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