4-Methoxybenzylamine → HCID 86699674, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(2,4,6-trichloropyrimidin-5-yl)acetate (43.3 g, 160.7 mmol) in N,N-dimethylformamide (500 mL) was added 4-Methoxybenzylamine (24.2 g, 176.8 mmol) and N,N′-diisopropylethylamine (24.9 g, 192.9 mmol), the reaction mixture was heated to 60° C. for 1 h. Quenched with water, extracted with ethyl acetate, and the organic extracts were combined, washed with hydrochloride (1 N), brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the as a pale-yellow solid (27.1 g, yield 45.6%). 1H NMR (400 MHz, CDCl3) δ ppm 7.29 (dd, J=6.0, 3.9 Hz, 1H), 6.93-6.85 (m, 1H), 6.14 (s, 1H), 4.63 (d, J=5.3 Hz, 2H), 4.15 (q, J=7.1 Hz, 2H), 3.83 (s, 3H), 3.62 (s, 2H), 1.23 (t, J=7.1 Hz, 2H).

Provenance & Evidence