Benzyl Bromide → HCID 66802462, compound

Participants

Reaction Steps

To 2-N-methyl-2-N-phenyl-6-[5-(piperidin-4-yl)-1,2,4-oxadiazol-3-yl]-1,3,5-triazine-2,4-diamine hydrochloride (Intermediate 105, 0.100 g, 0.257 mmol) in DMF (2 mL) was added sodium hydride (60% dispersion in mineral oil, 0.012 g, 0.309 mmol) at 0 C and stirred for 5 min. Benzyl bromide (30.6 μL, 0.257 mmol) was added, the reaction mixture was warmed to room temperature and stirred for 18 h. The mixture was then heated at 45 C for 18 h and re-treated with benzyl bromide (30.6 L, 0.257 mmol). The mixture was then heated at 50 C for 18 h and stirred room temperature for 72 h. The reaction mixture was diluted with DCM and then washed with a saturated aqueous solution of sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude compound was purified by preparative HPLC, Method A, to afford the title compound (2.2 mg, 1.9%).

Provenance & Evidence