Dimethylformamide → 1-Ethyl-3-(4-(4-morpholino-7-(pyrimidine-2-carbonyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

Participants

Reaction Conditions

Reaction Steps

Sodium pyrimidine-2-carboxylate (0.0229 g, 0.000157 mol) in dry N,N-Dimethylformamide (0.910 mL, 0.0118 mol) was added 1-Hydroxybenzotriazole (0.0313 g, 0.000232 mol) followed by N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.0409 g, 0.000213 mol) then followed by N,N-Diisopropylethylamine (0.0570 mL, 0.000327 mol) and then 1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0493 g, 0.000129 mol). The reaction mixture was stirred overnight. The reaction mixture was heated at 40° C. and stirred for 4 days. The reaction mixture was concentrated, chromatographed through silica gel (4 g, 0-10% MeOH in dichloromethane), and purified by HPLC. 1H NMR (500 MHz, DMSO) δ 8.99-8.94 (m, 1H), 8.68 (d, J=17.8, 1H), 8.24-8.06 (m, 2H), 7.66 (td, J=5.0, 2.2, 1H), 7.54-7.39 (m, 2H), 6.22-6.11 (m, 1H), 4.77 (s, 1H), 4.38 (s, 1H), 3.89 (d, J=5.2, 1H), 3.72 (dd, J=10.3, 5.7, 4H), 3.49 (dd, J=19.3, 4.3, 4H), 3.40 (d, J=5.3, 1H), 3.20-3.03 (m, 2H), 2.80 (s, 1H), 2.69 (s, 1H), 1.13-0.98 (m, 3H). LC/MS-m/z+489.2 (M+H)+.

Provenance & Evidence