Dimethylformamide → HCID 59239156, compound

Participants

Reaction Conditions

Reaction Steps

(S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.100 g, 0.252 mmol) in dry N,N-Dimethylformamide (1.00 mL, 12.9 mmol) at 0° C. was added tetrahydro-2H-pyran-4-carbaldehyde (0.02752 mL, 0.2522 mmol). The reaction mixture was stirred at 50° C. for 15 minutes then cooled at 0° C. and added Sodium triacetoxyborohydride (0.1069 g, 0.5044 mmol). The reaction mixture was allowed to warm slowly to room temperature and stirred for 2 hours. LC-MS shows mostly product. The reaction mixture was concentrated, chromatographed through silica gel (40 g, 0-5% MeOH in dichloromethane), and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.62 (s, 1H), 8.15 (d, J=8.7, 2H), 7.46 (d, J=8.7, 2H), 6.16 (t, J=5.5, 1H), 4.13 (d, J=6.7, 1H), 3.85 (t, J=9.0, 3H), 3.70 (d, J=9.0, 1H), 3.61 (dd, J=12.3, 4.0, 4H), 3.52-3.31 (m, 4H), 3.17-3.07 (m, 2H), 2.67 (s, 3H), 2.51 (m, 1H), 2.34 (d, J=7.3, 2H), 1.90 (d, J=7.3, 1H), 1.66 (d, J=12.6, 2H), 1.28-1.10 (m, 5H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+495.3 (M+H)+.

Provenance & Evidence