Cesium carbonate → 6-(4-chlorophenyl)-3-{4-[2-(ethyl-3-methylanilino)ethoxy]-3-methoxyphenyl}thieno[3,2-d]pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one (96 mg, 0.25 mmol, the preparation of which can be found in the section detailing the preparation of Example K1) in DMF was added N-(2-chloroethyl)-N-ethyl-3-methylaniline (99 mg, 0.50 mmol) and cesium carbonate (0.24 g, 0.75 mmol) and the mixture was stirred with heating at 75° C. for 12 h. The reaction was allowed to cool and 10 mL solution of 20% water/ethanol was added. The resulting precipitate was filtered and dried in a vacuum oven to give the title compound (58 mg, 42%). 1H NMR (DMSO-D6) δ 1.13 (3H, t, J=7.0 Hz), 2.24 (3H, s), 3.45 (2H, q, J=7.0 Hz), 3.70 (2H, d, J=5.8 Hz), 3.79 (3H, s), 4.16 (2H, d, J=5.8 Hz), 6.43 (1H, t, J=7.3 Hz), 6.57 (2H, m), 7.02-7.20 (4H, m), 7.60 (2H, d, J=8.6 Hz), 7.96 (3H, m), 8.39 (1H, s). LCMS m/z=546 (m+H+).

Provenance & Evidence