Methanol → (5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (1.0 g, 1.731 mmol) in dichloromethane (20 mL, 306 mmol) and methanol (20 mL, 494 mmol) was stirred at 0° C. and treated in portions with sodium borohydride powder (Aldrich) (0.211 g, 5.57 mmol). The resulting suspension was warmed up to room temperature and stirred for 1 h. The reaction mixture was treated with saturated NH4Cl (10 mL), diluted with water (40 mL) and stirred at room temperature for 2 h. The reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to give (5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methanol (0.850 g, 1.466 mmol, 85% yield). m/z (ESI, +ve ion) 580.2 (M+H)+.

Provenance & Evidence