Cyanuric chloride → 4-chloro-N-(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of cyanuric chloride (3.69 g, 20 mmol) in DCM (100 mL) at −10° C. was added methylmagnesium bromide (20 mL, 60 mmol, 3.0M solution in ether) maintaining the temperature at −10° C. The reaction was stirred for 4 h at −10° C. and then quenched with saturated ammonium chloride solution (20 mL). The organic layer was separated, dried (MgSO4) and filtered. The filtrate was cooled to 0° C. before the addition of 4-methoxybenzylamine (2.74 g, 20 mmol) and DIPEA (2.6 g, 20 mmol) took place. The reaction was stirred for 18 h at r.t. The organic layer was washed with water (2×20 mL), separated, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was crystallised from diisopropyl ether affording the title compound as a pale yellow solid (2.8 g, 51%). δH (CDCl3) 7.23 (d, J 9.2 Hz, 2H), 6.85 (d, J 9.2 Hz, 2H), 5.62 (br s, 1H), 4.56 (d, J 8.1 Hz, 2H), 3.79 (s, 3H), 2.38 (s, 3H). LCMS (ES+) 265 (M+H)+, RT 2.80 minutes (Method 5).

Provenance & Evidence