2-Chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl chloride → 1-(2-Chloro-4-(trifluoromethyl)pyrimidin-5-yl)ethanone

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Reaction Steps

To a solution of 2-chloro-4-trifluoromethylpyrimidine-5-carbonyl chloride (0.50 g, 2.0 mmol) in THF at -78° C. under N2 was added MeMgBr (0.75 ml, 2.3 mmol). The reaction was stirred 0.75 h, quenched with H2O (1 ml) and diluted with EtOAc (30 ml). The organic layer was washed with H2O, brine and then dried over MgSO4. The residue was chromatographed (SiO2, hexanes/EtOAc, 2:1) to provide the 5-acetyl-2-chloro-4-trifluoromethylpyrimidine (0.20 g) in 43% yield. The title compound was then prepared as described for ethyl 2-[N-(1'-aminocitraconamide)]-4-trifluoromethylpyrimidine-5-carboxylate of Example 20, resulting in a 29% yield (0.08 g); m.p. 61°-62° C.

Provenance & Evidence