Methylamine → 5-{4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}-N-methylnicotinamide

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Reaction Steps

Methyl 5-{4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinate (0.010 g, 0.023 mmol) and methylamine (0.124 g, 0.004 mol) were mixed in 1-butanol (2.00 mL) and the resulting mixture subjected to microwave radiation for 2000 seconds at 170° C., followed by irradiation for 4000 seconds at 180° C. The solvent was removed by evaporation, and the product purified by preparative HPLC to give 2 mg (20%) 5-{4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}-N-methylnicotinamide hydroformate as a white solid. MS [M+H]=437.1, LC/MS (EI) tR 3.55 min (Method D), 1H NMR (10% MeOD/CDCl3) δ (ppm) 8.93 (s, 1H), 8.43 (s, 1H), 8.20 (s, 1H), 7.70 (s, 1H), 7.60 (s, 1H), 7.40-7.28 (m, 4H), 7.11 (t, J=8.7 Hz, 2H), 3.84 (t, J=6.0 Hz, 2H), 2.95 (d, J=3.6 Hz, 3H), 2.67 (t, J=7.2 Hz, 2H), 1.75-1.59 (m, 2H), 1.59-1.45 (m, 2H)

Provenance & Evidence