N-(4-methyl-3-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine → N-(3-amino-4-methylphenyl)-4-(pyridin-3-yl)-2-pyrimidine-amine

Participants

Reaction Steps

N-(4-methyl-3-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine (34 g, 0.11 mol) and stannous chloride dihydrate (124.5 g, 0.55 mol) were dissolved in a solvent mixture of ethyl acetate and ethanol (300 ml, 10/1, v/v) and reacted under reflux for 26 hours. The reaction mixture was cooled to room temperature, washed with 10% aqueous hydrochloric acid solution, concentrated, and subjected to column chromatography (chloroform/methanol=9/1, v/v) to give N-(3-amino-4-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine (32 g).

Provenance & Evidence