3-Aminopropionitrile → HCID 59239379, compound

Participants

Reaction Conditions

Reaction Steps

(S)-4-(4-(3-methylmorpholino)-7-(pyrimidin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)aniline (0.0700 g, 0.000173 mol) in dry 1,4-Dioxane (1.50 mL, 0.0192 mol) was added Triethylamine (0.0266 mL, 0.000191 mol) followed by 20% Phosgene in toluene (1:4, Phosgene:Toluene, 0.100 mL). The reaction mixture was heated at 50° C. for 1 hour. The reaction mixture was cooled to room temperature and then added β-Cyanoethylamine (0.0764 mL, 0.00104 mol). The reaction mixture was stirred overnight. The reaction mixture was concentrated and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.94 (s, 1H), 8.56 (s, 1H), 8.22 (d, J=8.8, 2H), 8.17 (s, 1H), 7.52 (d, J=8.8, 2H), 6.96 (d, J=5.5, 1H), 6.58 (t, J=5.9, 1H), 4.76 (d, J=18.3, 1H), 4.65 (d, J=18.0, 1H), 4.13 (d, J=6.6, 1H), 3.99 (s, 1H), 3.88 (d, J=11.3, 1H), 3.81-3.55 (m, 7H), 3.46-3.32 (m, 1H), 2.74 (d, J=10.3, 2H), 2.70 (t, J=6.4, 2H), 1.26 (d, J=6.6, 3H). LC/MS-m/z+500.3 (M+H)+.

Provenance & Evidence