Hydrochloric Acid → 6-(5-Chloro-2-methoxy-phenyl)-N*4*-(4-trifluoromethylphenyl)-pyrimidine-2,4-diamine

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To a stirred suspension of 4-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-2-yl-amine (0.050 g, 0.185 mmol) in ethanol (7.5 ml) was added a solution of hydrogen chloride in dioxane (4.0 M, 0.03 ml) followed by 4-(trifluoromethyl)aniline (0.06 g, 0.37 mmol). The mixture was stirred under reflux for 45 minutes. After evaporation of volatiles under reduced pressure, the residue was treated with 1.0 M hydrochloric acid (10 ml) and stirred for 30 min. Filtration provided the hydrochloride salt of the title compound which was dissolved in methanol (10 ml). A solution of sodium carbonate in water (1.0 M, 1 ml) was added. After stirring for 1 hour, volatiles were evaporated under reduced pressure. The crude product was treated with water (10 ml) and stirred for 15 minutes. Filtration provided the title compound (0.053 g, 74% yield) as a white powder. 1H NMR (DMSO-d6) δ 3.90 (s, 3H, CH3), 6.44 (s, 2H, NH2), 6.81 (s, 1H, Ar), 7.19 (d, 1H, J=8.8 Hz, Ar), 7.46 (dd, 1H, J=8.8 Hz, J=2.6 Hz, Ar), 7.61 (d, 2H, J=8.5 Hz, Ar), 7.94 (d, 1H, J=2.6 Hz, Ar), 7.26 (d, 2H, J=8.5 Hz, Ar), 9.63 (s, 1H, NH).

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