4-Chloroaniline → Ethyl 2-(4-chlorophenylamino)pyrimidine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 2-chloropyrimidine-5-carboxylate (0.5 g, 2.68 mmol) and 4-chloroaniline (0.684 g, 5.36 mmol) in dioxane (15 mL) was heated at 100° C. for 8 h, diluted with ethyl acetate and filtered. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using 0-30% ethyl acetate in hexanes. The desired fractions were concentrated to give ethyl 2-(4-chlorophenylamino)pyrimidine-5-carboxylate as an orange solid (0.43 g, 58%). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.96 (2H, s), 7.57-7.64 (2H, m), 7.45 (1H, br. s.), 7.29-7.36 (2H, m), 4.37 (2H, q, J=7.02 Hz), 1.38 (3H, t, J=7.02 Hz). LCMS: R.T.=4.16 min; [M+H]+=277.96.

Provenance & Evidence