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

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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 may be found in Example K1) in DMF was added 2-(methylanilino)ethyl toluenesulfonate (153 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 a 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 (104 mg, 80%). 1H NMR (DMSO-D6) δ 3.01 (3H, s), 3.78 (5H, m), 4.18 (2H, t, J=3.7 Hz), 6.63 (1H, t, J=7.3 Hz), 6.78 (2H, d, J=7.2 Hz), 7.02-7.20 (5H, m), 7.60 (2H, d, J=8.6 Hz), 7.96 (3H, m), 8.39 (1H, s). LCMS m/z=518 (m+H+). Calcd. for C28H24ClN3O3S×1H2O: C, 62.74; H, 4.89; N, 7.84. Found: C, 62.76; H, 4.65; N, 7.82.

Provenance & Evidence