Diethyl Oxalate → HCID 9844340, compound

Participants

Reaction Steps

A mixture of 0.354 g (1 mmol) of 5-amino-4-(cyclopentylamino)-2-[[4-(morpholin-4-yl)phenyl]amino]pyrimidine and 5 mL (32 mmol) of diethyl oxalate in 20 mL of 2-ethoxyethanol is heated under reflux for 3 hours and then cooled to give 0.20 g (49%) of the title compound (Compound 23): mp (EtOH) 283–286° C. 1H NMR [(CD3)2SO]: δ 11.87 (br, 1H, exchangeable with D2O, H-5), 9.29 (br, 1H, exchangeable with D2O, 2NH), 8.12 (s, 1H, H-4), 7.50 (br d, J=9.0 Hz, 2H, H-2′,6′), 6.90 (d, J=9.1 Hz, 2H, H-3′,5′), 5.62 (pentet, J=8.8 Hz, 1H cyclopentyl CH), 3.74 (br t, J=4.7 Hz, 4H, CH2O)), 3.03 (br t, J=4.7 Hz, 4H, CH2N), 2.21–2.11 (m, 2H, cyclopentyl), 1.97–1.84 (m, 2H, cyclopentyl), 1.84–1.74 (m, 2H, cyclopentyl), 1.63–1.52 (m, 2H, cyclopentyl).

Provenance & Evidence