4-Chloroaniline → 6-(5-Chloro-2-methoxy-phenyl)-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamine

Participants

Reaction Steps

To a stirred suspension of the hydrochloride salt of 2-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-4-yl-amine (0.023 g, 0.075 mmol) in ethanol (7.0 ml) was added 4-chloroaniline (0.025 g, 0.20 mmol). The mixture was stirred under reflux for 6 hours. After evaporation of the solvent under reduced pressure, the residue was treated with hydrochloric acid (1.0 M, 10 ml) and stirred for 30 minutes. Filtration provided the hydrochloride salt of 6-(5-chloro-2-methoxy-phenyl)-N*2*-(4-chloro-phenyl)-pyrimidine-2,4-diamine which was treated with methanol (10 ml) and stirred while a solution of sodium carbonate in water (1.0 M, 1 ml) was added. After stirring for 1 hour, solvents were evaporated under reduced pressure. The residual solid was treated with water (10 ml) and stirred for 15 minutes. Filtration provided the title compound (0.019 g, 70% yield) as a white powder. 1H NMR (CDCl3) δ 4.80 (s, 2H, NH2), 6.62 (s, 1H, Ar), 6.94 (d, 1H, J=8.8 Hz, Ar), 6.98 (s, 1H, NH), 7.27-7.30 (m, 2H, Ar), 7.36 (dd, 1H, J=8.8 Hz, J=2.8 Hz, Ar), 7.61-7.63 (m, 2H, Ar), 7.93 (d, 1H, J=2.8 Hz, Ar),

Provenance & Evidence