Toluene → HCID 59351598, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloropyrimidine-2,4(1H,3H)-dione (5 g), 4′-(bromomethyl)-3′-fluorobiphenyl-2-carbonitrile (9.9 g), potassium carbonate (2.36 g) and dimethyl sulfoxide (35 mL) was stirred at 65° C. for 2 hr. To the reaction mixture were added 1N aqueous sodium hydroxide solution (35 mL) and toluene (30 mL), and the mixture was cooled to 0° C. The precipitated solid was dissolved in chloroform, and the mixture was extracted with 1N hydrochloric acid. The obtained chloroform layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in n-propanol (60 mL), a solution of sodium (0.58 g) in n-propanol (30 mL) was added, and the mixture was stirred at 100° C. for 16 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with 1N aqueous sodium hydroxide solution (50 mL) and ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC to give the title compound as a colorless solid (0.55 g, 26%).

Provenance & Evidence