2-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine → Imatinib amine

Participants

Reaction Steps

A suspension of 143.0 g (0.46 mol) of N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine in 7.15 liters of ethyl acetate is stirred with 14.3 g of palladium on active carbon (10% Pd) under a hydrogen atmosphere at normal pressure for 6.5 hours. The suspension is filtered and the filtrate is concentrated in a rotary evaporator. The crude product is recrystallised from methylene chloride, yielding N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine; m.p. 138° C.-140° C., Rf=0.36 (methylene chloride:methanol=9:1).

Provenance & Evidence