Cesium carbonate → 3-(4-{2-[4-chloro(methyl)anilino]ethoxy}-3-methoxyphenyl)-6-(4-chlorophenyl)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 2-[4-chloro(methyl)anilino]ethyl p-toluenesulfonate (170 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 (136 mg, 98%). 1H NMR (DMSO-D6) δ 3.00 (3H, s), 3.77 (5H, m), 4.21 (2H, m), 6.81 (2H, d, J=9.0 Hz), 7.02-7.20 (5H, m), 7.58 (2H, d, J=8.6 Hz), 7.95 (3H, m), 8.39 (1H, s). Calcd. for C28H23Cl2N3O3S×3HCl: C, 50.81; H, 3.96; N; 6.35. Found: C, 50.91; H, 3.95; N, 6.23.

Provenance & Evidence