Phosgene → HCID 59239567, compound

Participants

Reaction Conditions

Reaction Steps

Step 3—Synthesis of compound uv: (S)-2-(4-aminophenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carbaldehyde (0.100 g, 0.000283 mol) in dry 1,4-Dioxane (2.00 mL, 0.0256 mol) was added Triethylamine (0.0434 mL, 0.000311 mol) followed by 20% Phosgene in toluene (1:4, Phosgene:Toluene, 0.170 mL). The reaction mixture was heated at 50° C. for 1 hour. The reaction mixture was cooled to room temperature and then added 2,2,2-trifluoroethylamine (0.1340 mL, 0.001703 mol). The reaction mixture was stirred overnight. The reaction mixture was concentrated and purified by HPLC. 1H NMR (500 MHz, DMSO) δ 9.01 (s, 1H), 8.27-8.17 (m, 3H), 7.52 (d, J=8.8, 2H), 6.81 (d, J=6.5, 1H), 4.66-4.39 (m, 2H), 4.08 (s, 1H), 3.93 (ddd, J=31.8, 19.1, 10.1, 3H), 3.78-3.53 (m, 6H), 3.50-3.40 (m, 2H), 2.73 (s, 1H), 2.64 (s, 1H), 1.25 (t, J=7.4, 3H). LC/MS-m/z+479.2 (M+H)+

Provenance & Evidence