Diisobutylaluminumhydride → 2-Chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde

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Reaction Conditions

Reaction Steps

Diisobutyl aluminum hydride (1.21 mL, 1M solution in hexane, 1.22 mmol), was added dropwise to a solution of ethyl 2-chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carboxylate (242 mg, 0.81 mmol) in dry dichloromethane (10 mL) under nitrogen at −78° C. The mixture was stirred at −78° C. for 1 h. Diisobutyl aluminum hydride solution (1 mL) was added and the mixture was stirred for 15 minutes. The mixture was quenched with methanol and allowed to reach ambient temperature. Water (10 mL) and dichloromethane were added, the pH of the water phase was adjusted to 6 by addition of acetic acid. The mixture was filtered through a pad of silica gel and sodium bicarbonate. The water phase was extracted with 5% solution of methanol in dichloromethane (3×10 mL). The combined organic phase was dried over sodium sulfate and concentrated in vacuum to yield the title product, 216 mg (100%).

Provenance & Evidence