Dichloromethane → 2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine-4-carbaldehyde

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Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carboxylate (0.49 g, 1.05 mmol) in dry dichloromethane (25 mL) diisobutyl aluminum hydride (2.63 mL, 1M solution in hexane, 2.63 mmol), was added under nitrogen during 10 min at −78° C. The mixture was stirred at −78° C. for 1 h. Diisobutyl aluminum hydride solution (2.8 mL) was added and the mixture was stirred for 10 min. The mixture was quenched with methanol and allowed to warm to ambient temperature. Water (5 mL) was added, the slurry was stirred for 20 min and filtered through a pad of diatomeous earth. The pad was washed with 10% solution of methanol in dichloromethane. The organic phase was separated and the water phase was extracted with 10% solution of methanol in dichloromethane. The combined organic extracts was dried over sodium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica eluting with 0-5% gradient of methanol in dichloromethane to yield the title compounds, 318 mg (72%).

Provenance & Evidence