Acetic Acid → 5-{4-[5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinic acid

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Reaction Steps

A mixture of methyl-5-{4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinate (0.010 g, 0.023 mmol) and potassium hydroxide (0.0112 g, 0.200 mmol) in methanol (0.5 mL) was stirred at room temperature for 12 h. Acetic acid (200 mg, 3.33 mmol) was then added, and the reaction solvent was removed by evaporation. The product was purified by column chromatography over silica gel using 5% methanol in dichloromethane as eluant to afford 8 g (83%) 5-{4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinic acid hydroformate as white solid. MS [M+H]=424.1, LC/MS (EI) tR 3.89 min (Method D), 1H NMR (10% MeOD/CDCl3) δ (ppm) 8.94 (s, 1H), 8.73 (s, 1H), 8.28 (s, 1H), 7.68 (s, 1H), 7.40-7.30 (m, 3H), 7.10 (t, J=8.4 Hz, 2H), 3.84 (t, J=6.3 Hz, 2H), 2.68 (t, J=7.2 Hz, 2H), 1.75-1.59 (m, 2H), 1.59-1.45 (m, 2H)

Provenance & Evidence