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

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Reaction Conditions

Reaction Steps

Methylmagnesium bromide (1.4 M in 3:1 toluene/THF) (Aldrich, St. Louis, Mo.; 1.787 mL, 2.502 mmol) was added (dropwise, over 10 min) to a yellow-brown solution of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde (Example 144, Step 1; 451.7 mg, 0.782 mmol) in THF (5.0 mL) at 0° C., and the resulting brown solution was stirred at 0° C. for 1 h. Saturated ammonium chloride (10 ml) and water (10 ml) were then added, THF was removed in vacuo, and the resulting mixture was extracted with EtOAc (2×60 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Trituration of the residue with hexanes (10 mL) furnished 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol (331.1 mg, 0.558 mmol, 71.3% yield) as a yellow-brown solid. m/z (ESI, +ve) 594.2 (M+H)+.

Provenance & Evidence