4-(5-(Benzyloxy)-2-fluoropyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine → 5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)-6-fluoropyridin-3-OL

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A solution of 4-(5-(benzyloxy)-2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.080 g, 0.145 mmol) in EtOAc (8 mL) under N2 gas was treated with 10% palladium on carbon (Aldrich) (7.72 mg, 0.073 mmol). The reaction mixture was purged with N2 and then stirred at rt under H2 for 2 h. The reaction mixture was passed through Celite® (diatomaceous earth). The filtrate was concentrated. The crude product was purified by column chromatography (12 g, 20% to 30% acetone in hexanes) to give the product as a white solid (0.050 g). m/z (ESI, +ve ion) 462.0 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 8.03 (dd, J=7.60, 3.07 Hz, 1H); 7.89 (br. s., 1H); 7.23 (d, J=6.43 Hz, 4H); 6.87 (t, J=7.53 Hz, 4H); 5.78 (br. s., 1H); 4.82 (s, 4H); 3.81 (d, J=4.82 Hz, 6H); 2.55 (s, 3H).

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