Phosgene → HCID 59239569, 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 3-aminoisoxazole (0.0770 mL, 0.00104 mol). The reaction mixture was stirred overnight. The reaction mixture was concentrated and purified by HPLC. 1H NMR (500 MHz, DMSO) δ 9.70 (s, 1H), 9.16 (s, 1H), 8.77 (d, J=1.6, 1H), 8.67 (s, 1H), 8.29 (t, J=7.5, 3H), 7.58 (d, J=8.8, 2H), 7.11 (d, J=6.4, 1H), 6.88 (d, J=1.7, 1H), 4.85 (d, J=18.4, 1H), 4.74 (d, J=18.5, 1H), 4.15 (d, J=6.1, 1H), 4.06 (s, 1H), 3.92-3.82 (m, 3H), 3.76-3.54 (m, 4H), 3.48-3.41 (m, 2H), 2.79 (s, 2H), 1.27 (d, J=6.7, 3H). LC/MS-m/z+514.2 (M+H)+

Provenance & Evidence