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 aminocyclobutane (0.0892 mL, 0.00104 mol). The reaction mixture was stirred overnight. LC-MS shows mostly product. The reaction mixture was concentrated purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.65 (s, 1H), 8.56 (s, 1H), 8.22 (dd, J=16.1, 7.5, 3H), 7.48 (d, J=8.8, 2H), 6.96 (d, J=6.2, 1H), 6.57 (d, J=7.6, 1H), 4.76 (d, J=18.0, 1H), 4.64 (d, J=18.3, 1H), 4.15 (dt, J=15.6, 7.8, 2H), 4.00 (dd, J=16.4, 8.3, 1H), 3.87 (d, J=11.3, 1H), 3.80-3.57 (m, 5H), 2.75 (s, 2H), 2.20 (dt, J=14.1, 5.0, 2H), 2.10 (ddd, J=10.1, 7.6, 3.6, 1H), 1.93-1.79 (m, 2H), 1.73 (dt, J=11.9, 9.7, 1H), 1.56 (m, 2H), 1.26 (d, J=6.6, 3H). LC/MS-m/z+501.3 (M+H)+
