4-(Difluoromethoxy)aniline → Ethyl 2-((4-(difluoromethoxy)phenyl)amino)-4-methoxypyrimidine-5-carboxylate

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A mixture of 4-(difluoromethoxy)aniline (0.285 mL, 2.305 mmol) and ethyl 4-methoxy-2-(methylsulfonyl)pyrimidine-5-carboxylate (0.4 g, 1.537 mmol) in dioxane was heated in the microwave at 150° C. for 50 min. The mixture was then cooled to room temperature and concentrated. The residue was purified by flash chromatography on silica gel using 5-50% ethyl acetate in hexanes. The desired fractions were concentrated to give ethyl 2-((4-(difluoromethoxy)phenyl)amino)-4-methoxypyrimidine-5-carboxylate as an orange solid (0.37 g, 71%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.83 (s, 1H), 7.67-7.58 (m, 2H), 7.37 (br. s., 1H), 7.20-7.09 (m, 2H), 6.74-6.12 (m, 1H), 4.35 (q, J=7.0 Hz, 2H), 4.08 (s, 3H), 1.38 (t, J=7.0 Hz, 3H). LCMS: R.T.=0.96; [M+H]+=340.1.

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