Nitrogen → 4-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

In a screw top flask, 4,6-dichloropyrimidine (3.1 g, 21 mmol), 4-trifluoromethyl-phenyl boronic acid (3.9 g, 21 mmol) and potassium phosphate (8.8 g, 42 mmol) were combined in dimethoxyethane (60 mL) and water (12 mL). The flask was flushed with N2 and tetrakis(triphenylphosphine)palladium (1.2 g, 1.0 mmol) was added. The flask was sealed and heated to 90° C. for 12 hours. The reaction mixture was cooled to rt and H2O (50 mL) was added and resulting mixture was extracted with EtOAc (3×50 mL). The organic phases were combined, washed with brine (50 mL), dried with Na2SO4, filtered, and concentrated. The resulting residue was purified by flash column chromatography using ethyl acetate-hexanes (0%-20%) to provide a clear oil (2.6 g, 48%). MS (ESI): mass calcd. for C11H6ClF3N2, 258.0; m/z found 259.1 [M+H]+.

Provenance & Evidence