Reaction Steps
(S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0995 g, 0.251 mmol) in dry was added 1-(pyridin-3-ylmethyl)piperidin-4-one (0.0486 g, 0.255 mmol). The reaction mixture was then heated at 70° C. for 40 min. The reaction mixture was then cooled at 0° C. and added Sodium triacetoxyborohydride (0.1118 g, 0.5275 mmol). The reaction mixture was allowed to warm slowly to room temperature and stirred for 3 days. The reaction mixture was diluted with water, extracted three times with 10% MeOH in dichloromethane, dried over Magnesium sulfate, filtered, evaporated, chromatographed through silica gel (12 g, 0-10% MeOH in dichloromethane followed by 6:2:1:1 EtOAc:acetone:water:MeOH), and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.61 (s, 1H), 8.49 (d, J=1.7, 1H), 8.46 (dd, J=4.8, 1.6, 1H), 8.15 (d, J=8.8, 2H), 7.71 (d, J=7.8, 1H), 7.46 (d, J=8.8, 2H), 7.36 (dd, J=7.7, 4.8, 1H), 6.15 (t, J=5.6, 1H), 4.12 (d, J=6.5, 1H), 3.91-3.81 (m, 1H), 3.77-3.53 (m, 6H), 3.50 (s, 2H), 3.45-3.34 (m, 1H), 3.17-3.06 (m, 2H), 2.86 (d, J=11.0, 2H), 2.81-2.71 (m, 1H), 2.70-2.56 (m, 3H), 2.39 (t, J=11.3, 1H), 2.01 (t, J=10.8, 2H), 1.83 (s, 2H), 1.60-1.42 (m, 2H), 1.22 (d, J=6.6, 3H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+571.3 (M+H)+.
