Phosgene → HCID 59239501, compound

Participants

Reaction Conditions

Reaction Steps

(S)-4-(4-(3-methylmorpholino)-7-(pyrimidin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)aniline (0.0795 g, 0.000197 mol) in dry 1,4-Dioxane (1.50 mL, 0.0192 mol) was added Triethylamine (0.0302 mL, 0.000217 mol) followed by 20% Phosgene in toluene (1:4, Phosgene:Toluene, 0.120 mL). The reaction mixture was heated at 50° C. for 1 hour. The reaction mixture was cooled to room temperature and then added 3-aminoisoxazole (0.0874 mL, 0.00118 mol). The reaction mixture was stirred overnight. The reaction mixture was concentrated and purified by HPLC. 1H NMR (500 MHz, DMSO) δ 9.69 (s, 1H), 9.12 (s, 1H), 8.74 (d, J=1.6, 1H), 8.44 (d, J=4.7, 2H), 8.28 (d, J=8.7, 2H), 7.57 (d, J=8.7, 2H), 6.87 (d, J=1.7, 1H), 6.69 (t, J=4.7, 1H), 4.91 (d, J=18.6, 1H), 4.75 (d, J=18.7, 1H), 4.18-4.09 (m, 2H), 3.86 (dd, J=17.0, 9.4, 2H), 3.73-3.69 (m, 1H), 3.66-3.58 (m, 3H), 3.43 (t, J=10.8, 1H), 2.75 (s, 2H), 1.26 (d, J=6.7, 3H). LC/MS-m/z+514.2 (M+H)+.

Provenance & Evidence