Sodium Carbonate → 4-chloro-5-methyl-6-[4-(trifluoromethyl)phenyl]Pyrimidine

Participants

Reaction Steps

To a solution of 4,6-dichloro-5-methylpyrimidine (1 g, 6.13 mmol) in dimethoxyethane (28 mL) and water (14 mL) was added sodium carbonate (1.69 g, 16.0 mmol), 4-trifluoromethylphenylboronic acid (1.165 g, 6.13 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.14 g). The resulting mixture was heated at reflux under nitrogen for 18 h, the reaction mixture was allowed to cool to room temperature and diluted with water (100 mL) before extraction into CHCl3 (2×100 mL). The organic solution separated by hydrophobic frit and the solvents removed in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) eluting with 19:1 cyclohexane:EtOAc afforded the title compound as a white solid (1.1 g).

Provenance & Evidence