Water → 6-chloro-N,N-bis(4-methoxybenzyl)-2-methylpyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60 wt % in mineral oil) (0.340 g, 8.51 mmol) was added in one portion to a mixture of 6-chloro-N-(4-methoxybenzyl)-2-methylpyrimidin-4-amine (1.87 g, 7.09 mmol) and 1-(chloromethyl)-4-methoxybenzene (1.059 mL, 7.80 mmol) in DMF (50 mL) at 0° C. The resulting mixture was stirred at 0° C. for 5 min and then was warmed to 25° C. and stirred for 2 h. Water (200 mL) was then added, and the precipitated solid was collected by vacuum filtration, washed with water (150 mL), and dried in vacuo to furnish 6-chloro-N,N-bis(4-methoxybenzyl)-2-methylpyrimidin-4-amine (2.69 g, 7.01 mmol, 99% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.11 (d, J=7.24 Hz, 4H); 6.86 (d, J=7.24 Hz, 4H); 6.26 (s, 1H); 4.65 (br. s., 4H); 3.80 (s, 6H); 2.53 (s, 3H). m/z (ESI, +ve ion) 384.1 (M+H)+.

Provenance & Evidence