Pyridine → HCID 68805818, compound

Participants

Reaction Steps

To a solution of N-(4-bromo-2,6-dimethylphenyl)-2-chloro-6-methyl-5-nitropyrimidin-4-amine (18.5 g, 49.8 mmol) and 4-aminobenzonitrile (5.9 g, 49.8 mmol) in THF (250 ml) at ambient temperature was added pyridine (4.0 ml, 49.8 mmol). The reaction mixture was heated to reflux and stirred for 2 days under argon. Upon completion half of the solvent was removed in vacuo. The solids were dissolved in methanol and 250 ml brine was added. The aqueous layer was extracted with ethyl acetate (3×125 ml) and the collected organic fractions were dried with MgSO4, filtered and reduced in vacuo. The resulting solids were slurried in methanol and Et2O and filtered. The filtrand was washed 3× with cold Et2O and dried overnight under vacuum to give 14.4 g (64%) of methyl 4-(4-(4-bromo-2,6-dimethylphenylamino)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile as a brown powder. m/z=453 [M+1].

Provenance & Evidence