Methyl formate → 4-Ethoxy-6-(trifluoromethyl)pyrimidine-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of 5.76 g (21.3 mmoles) of 5-bromo-4-ethoxy-6-trifluoromethylpyrimidine dissolved in 250 ml of tetrahydrofuran was cooled to −78° C. Thereinto was dropwise added 22.6 ml of a 1.6 M hexane solution containing 36.1 mM of n-butyl lithium. The mixture was stirred for 40 minutes. Thereto was added 2.7 g (45.1 mmoles) of methyl formate. The mixture was stirred for 1.5 hours to give rise to a reaction. After the completion of the reaction, an aqueous ammonium chloride solution was added and extraction with ether was conducted. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate mixed solvent) to obtain 3.82 g (yield: 81.6%) of 4-ethoxy-6-trifluoromethylpyrimidine-5-carboaldehyde.

Provenance & Evidence