Acetic Acid → HCID 59548161, compound

Participants

Reaction Steps

4 Å molecular sieves were added to a mixture of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (0.300 g, 0.519 mmol) and 3(S)-3-methylmorpholine (0.158 mL, 1.558 mmol) in toluene (50 mL, 470 mmol) and the mixture was stirred under N2 at reflux for 3 h. The mixture was filtered through Celite® (diatomaceous earth) and concentrated in vacuo to give a yellow oil. The oil was dissolved in methanol (50 mL, 1234 mmol) at 0° C. and the stirred solution was treated with sodium cyanoborohydride (0.082 mL, 1.558 mmol). Glacial acetic acid (0.500 mL, 8.66 mmol) was added slowly. The mixture was allowed to warm up to room temperature and stirred for 3 h. The reaction was quenched with 20% NaOH aqueous solution (5 mL) and water (2 mL), extracted with EtOAc and dried over K2CO3, and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (40 g) eluting with gradient of 20% to 50% EtOAc/hexane to give (S)—N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-((3-methylmorpholino)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.095 g, 0.143 mmol, 27.6% yield). m/z (ESI, +ve ion) 663.3 (M+H)+.

Provenance & Evidence