Potassium Carbonate → N-(3-{3-[(5-phenylthieno[2,3-d]pyrimidin-4-yl)oxy]propoxy}phenyl)acetamide

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A mixture of 5-phenylthieno[2,3-d]pyrimidin-4(1H)-one (0.023 g, 0.10 mmol), N-[3-(3-bromopropoxy)phenyl]acetamide (0.0274 g, 0.10 mmol), potassium carbonate (0.0418 g, 0.30 mmol) and N,N-dimethylformamide (1.0 mL) was heated to 90° C. for 6 h. The reaction was then allowed to cool to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate (30 mL), water (30 mL) was added, and the organic layer was separated, Concentration, followed by followed by silica gel column chromatography purification (using 1.50% methanol in 1:1 ethyl acetate/hexane and ammonia (0.03%) as eluent) afforded N-(3-{3-[(5-phenylthieno[2,3-d]pyrimidin-4-yl)oxy]propoxy}phenyl)acetamide in 66% yield. N-{4-[3-(4-oxo-5-phenylthieno[2,3-d]pyrimidin-1(4H)-yl)propoxy]phenyl}acetamide was also formed in 12% yield during the reaction.

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