Carbon Dioxide → 2-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-dichloro-5-trifluoromethylpyrimidine (500 mg, 2.3 mmol) in dry CH3CN (40 mL) was added 2-amino-N-methylbenzamide (350 mg, 2.3 mmol) at room temperature. The reaction mixture was cooled to −30° C. using dry ice. Powdered KOH (1.0 g, 17.8 mmol) was added and the reaction mixture was stirred at −30° C. for 1 h, and then warmed to −10° C. to −5° C. and stirred for another 2 h, then quenched with water (200 mL). The mixture was extracted with EtOAc (3×100 mL), the combined organic layer was dried over MgSO4, concentrated, and residue was purified by column chromatography to give 213 mg of the title compound (yield: 28%). 1H NMR (DMSO, 400 MHz): δ=2.75 (d, J=4.4 Hz, 3H), 7.20-7.24 (m, 1H), 7.53-7.58 (m, 1H), 7.74 (dd, J=2.0, 8.0 Hz, 1H), 8.33 (dd, J=1.2, 8.4 Hz, 1H), 8.85 (s, br, 1H), 12.0 (s, br, 1H).

Provenance & Evidence