Reaction Steps
(S)-6-(benzyloxy)-N-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)pyridin-2-amine (0.2684 g, 0.5277 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.226 g, 0.704 mmol) and Formic acid (0.0294 mL, 0.779 mmol) were combined then added dry N,N-Dimethylformamide (2.20 mL, 28.4 mmol) followed by N,N-Diisopropylethylamine (0.507 mL, 2.91 mmol). The reaction mixture stirred for 1 hour then concentrated and chromatographed through silica gel (12 g, 0-5% MeOH in dichloromethane). 1H NMR (500 MHz, DMSO) δ 9.33 (s, 1H), 8.20 (dd, J=7.4, 5.2, 2H), 7.70-7.65 (m, 2H), 7.54 (t, J=7.9, 1H), 7.47 (d, J=7.7, 2H), 7.39 (t, J=7.5, 2H), 7.32 (t, J=7.2, 1H), 6.47 (d, J=7.9, 1H), 6.27 (d, J=7.7, 1H), 5.39 (s, 2H), 4.58 (dt, J=18.2, 12.9, 2H), 4.41 (d, J=19.0, 1H), 4.08 (s, 1H), 3.89 (d, J=11.5, 1H), 3.80-3.51 (m, 5H), 3.44 (s, 1H), 2.73 (s, 1H), 2.69 (s, 1H), 1.30-1.18 (m, 3H). LC/MS-m/z+537.4 (M+H)+.
