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

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Reaction Conditions

Reaction Steps

Sodium borohydride (103 mg, 2.72 mmol) was added to a suspension 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) (522.8 mg, 0.905 mmol) in a mixture of methanol (5.0 mL) and DCM (5.0 mL) at 0° C. The resulting solution was stirred at 0° C. for 5 min and then was allowed to warm to 25° C. and stir for 45 min. Saturated aqueous ammonium chloride (10 mL) and water (20 mL) were subsequently added, and the resulting mixture was extracted with DCM (2×50 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to provide (5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methanol (504.5 mg, 0.870 mmol, 96% yield) as a yellow-orange solid. m/z (ESI, +ve ion) 580.2 (M+H)+.

Provenance & Evidence