Hydrochloric Acid → HCID 11647546, compound

Participants

Reaction Steps

To a solution of 5-{3-[5-(4-fluorophenyl)-thieno[2,3-d]pyrimidin-4-yloxy]-propoxy}-nicotinic acid methyl ester (100 mg) in dioxane (10 mL) was added 0.80 M lithium hydroxide in water (2.0 mL). The reaction was stirred at ambient temperature for 16 hours, then acidified with 1M hydrochloric acid to pH 3, and the solvent removed under reduced pressure. The residue was dissolved in 20% methanol/dichloromethane (40 mL), filtered, and the filtrate was concentrated. The product was purified by column chromatography over silica gel using 10% methanol in dichloromethane as eluant to give 90 mg (93%) of 5-{3-[5-(4-fluorophenyl)-thieno[2,3-d]pyrimidin-4-yloxy]-propoxy}-nicotinic acid as a white solid. MS [M+H] 425.9, 1H NMR (CD3OD) δ (ppm) 8.91 (s, 1H), 8.63 (s, 1H), 8.62 (s, 1H), 8.27 (s, 1H), 7.60-7.45 (m, 3H), 7.10 (t, J=8.7 Hz, 2H), 4.67 (t, J=9.0 Hz, 2H), 3.94 (t, J=9.3 Hz, 2H), 2.22 (t, J=9.0 Hz, 2H).

Provenance & Evidence