Ammonia → 6-chloro-N-methyl-N-phenyl-[1,3,5]triazine-2,4-diamine

Participants

Reaction Steps

To a stirred solution of (4,6-dichloro-[1,3,5]triazin-2-yl)-methyl-phenyl-amine (Intermediate 42, 2.7 g, 10.58 mmol) in THF (45 ml) was added a solution of conc. aqueous ammonia (3 ml, 52.91 mmol). The reaction was allowed to stir at room temperature for 1 h, the reaction was then diluted with THF (50 ml), treated with conc. aqueous ammonia (1 ml, 17.64 mmol) and stirred for 18 h. The reaction was concentrated under vacuum and taken up in DCM (150 ml); the solution was then extracted with 2M aq. HCl (2×50 mL), and saturated brine (20 mL) and dried further over anhydrous sodium sulfate. The organic phase was evaporated to dryness to furnish the product as an off white solid (2.743 g, 110%). Method B HPLC-MS: MH+ requires m/z=236. Found: m/z=236, Rt=1.76 min (88%). 1H NMR (500 MHz, CDCl3) δ ppm 7.09-7.44 (5H, m), 5.21-5.65 (2H, m), 3.40 (3H, s).

Provenance & Evidence