Ethanol → 2-Methyl-5-(4-trifluoromethyl-phenyl)-pyrimidine

Participants

Reaction Conditions

Reaction Steps

A solution of 7.95 g (75 mmol) of sodium carbonate in 15 ml of water was added to a mixture of 2.6 g (15 mmol) of 5-bromo-2-methylpyrimidine [Coll. Czech.Chem. Comm. 14 (1949), 223–235], of 4 g (21 mmol) of 4-(trifluoromethyl)benzeneboronic acid and of 0.52 g (0.45 mmol) of tetrakis(triphenylphosphine)palladium in a mixture of 50 ml of 1,2-dimethoxy-ethane and of 30 ml of ethanol. The reaction mixture was stirred at 80° C. for 2 hours; afterwards, it was concentrated by distilling off the major part of the organic solvents. Subsequently, the residue was extracted with 3 portions of tert.-butyl methyl ether. The combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate and finally evaporated. The residue was chromatographed on silicagel with a mixture of dichloromethane/tert.-butyl methyl ether (9/1 vol./vol.) as eluent. 3 g of the title compound was obtained as greenish solid.

Provenance & Evidence