Pyridine → 4-(4-(4-Bromo-2,6-dimethylphenylthio)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-bromo-2,6-dimethylphenylthio)-2-chloro-6-methyl-5-nitropyrimidine (59 mmol), 4-aminobenzonitrile (65 mmol) and pyridine (59 mmol) in THF (300 ml) is heated to 80° C. for 10 hours. The reaction mixture is dissolved in methanol, washed with brine and extracted with ethyl acetate. The organic layer is washed twice with brine, dried over MgSO4 and concentrated to dryness. The solid is washed with a mixture of hexane:ethyl acetate (80:20) before filtration. After filtration, the solid is washed again with methanol. The filtrate may be concentrated and additional rounds of precipitation performed following the same procedure, until all product is recovered. The combined solids are recrystallized from acetone.

Provenance & Evidence