Reaction Steps
(S)-1-ethyl-3-(4-(4-(3-ethylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0500 g, 0.122 mmol) in dry N,N-Dimethylformamide (0.593 mL, 7.66 mmol) at 0° C. was added 3-oxetanone (0.00881 mL, 0.122 mmol). The reaction mixture was stirred at 50° C. for 10 minutes then cooled at 0° C. and added Sodium triacetoxyborohydride (0.05163 g, 0.2436 mmol). The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was filtered through a disc filter and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.61 (s, 1H), 8.14 (d, J=8.7, 2H), 7.46 (d, J=8.7, 2H), 6.15 (t, J=5.5, 1H), 4.64 (t, J=6.2, 2H), 4.59-4.50 (m, 2H), 3.97 (s, 1H), 3.86 (d, J=10.7, 1H), 3.78 (d, J=11.2, 1H), 3.74-3.60 (m, 4H), 3.55 (t, J=10.9, 1H), 3.43 (d, J=10.4, 1H), 3.35 (d, J=17.0, 1H), 3.18-3.05 (m, 2H), 2.76 (s, 1H), 2.68 (d, J=11.2, 1H), 2.60 (d, J=15.2, 1H), 2.41-2.30 (m, 1H), 1.87-1.67 (m, 2H), 1.06 (t, J=7.2, 3H), 0.83 (t, J=7.4, 3H). LC/MS-m/z+467.2 (M+H)+.
