4-Methylmorpholine → HCID 178509063, compound

Participants

Reaction Steps

Solid portions of potassium-4-amino-2-tritylsulfanylpyrimidine-5-carboxylate (46 g, 10 mmol) followed by HATU (39 g, 0.10 mol) were added, at ambient temperature, to a solution of 4-fluoroaniline (11 g, 0.10 mol) and NMM (31 g, 0.30 mol) in NMP (500 mL). After stirring for 12 hours, the resulting orange solution was poured into water (1000 mL) and the oily, solid precipitant was collected, dissolved in dichloromethane (500 mL), and diluted with acetic acid (50 mL). The resulting solution was stirred (ambient temperature, 3 h), then concentrated in vacuo (to about 150 mL total volume) and diluted with diethyl ether (100 mL). The resulting yellow solid was collected, washed with dichloromethane and dried in vacuo to afford the titled compound (13 g, 49 mmol, 49% yield). 1H NMR (300 MHz, CD3OD) δ 8.20 (s, 1H), 7.58 (dd, J=9.3, 4.8 Hz, 2H), 7.07 (app. t, J=9.0 Hz, 2H); MS (+APCI) m/z 265 (MH+, 100).

Provenance & Evidence