1-(Bromomethyl)-3-chlorobenzene → 5-((1-(3-Chlorobenzyl)piperidin-4-yl)methoxy)quinazoline-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (2.5 g, 9.15 mmol) and diisopropylethylamine (2.96 g, 22.87 mmol) in DMF (16 mL) was added a solution of 3-chlorobenzyl bromide in DMF (4 mL). The reaction mixture was heated at 60° C. with stirring for 20 h. The mixture was concentrated, water was added stirred for 1 h. The precipitate was filtered, washed with water, dried. Purified by silica gel column chromatography using 3-10% methanol in dichloromethane afforded 1.82 g of 5-[1-(3-chlorobenzyl)piperidin-4-ylmethoxy]quinazoline-2,4-diamine 1H NMR (400 MHz, DMSO-d6) δ 7.25-7.38 (m, 5H), 7.2 (s, 2H), 6.77 (dd, J=8.0, 1.2 Hz, 1H), 6.53 (dd, J=8.0, 0.8 Hz, 1H), 5.95 (s, 2H), 3.99 (d, J=6.4 Hz, 2H), 3.48 (s, 2H), 2.84 (d, J=11.2 Hz, 2H), 1.7-2.07 (m, 5H), 1.3-1.42 9m, 2H). MS m/z (ESI) 399 (M+H)+.

Provenance & Evidence