Dimethylformamide → HCID 44815761, compound

Participants

Reaction Conditions

Reaction Steps

1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0499 g, 0.000130 mol) in dry N,N-Dimethylformamide (1.00 mL, 0.0129 mol) was cooled at 0° C. then added sodium hydride, 60% dispension in mineral oil (3:2, Sodium hydride:Mineral Oil, 0.0109 g), warmed to room temperature, stirred for 10 minutes, added 4-Chloro-6-methylpyrimidine (0.0196 g, 0.000152 mol) heated at 60° C. for 3 hours. LC-MS does show some product present but a lot of starting material is still remaining. The reaction mixture was heated at 60° C. and stirred overnight. The reaction mixture was filtered and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.64 (s, 1H), 8.44 (s, 1H), 8.21 (d, J=8.8, 2H), 7.49 (d, J=8.8, 2H), 6.86 (s, 1H), 6.16 (t, J=5.6, 1H), 4.69 (s, 2H), 3.87 (s, 2H), 3.79-3.68 (m, 4H), 3.48 (d, J=4.4, 4H), 3.20-3.05 (m, 2H), 2.75 (s, 2H), 2.30 (s, 3H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+475.3 (M+H)+

Provenance & Evidence