Acetic Acid → HCID 66612194, compound

Participants

Reaction Steps

A slurry of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)nicotinaldehyde (Example 143, 0.200 g, 0.336 mmol), manganese dioxide (0.584 g, 6.72 mmol), methanol (0.068 mL, 1.679 mmol), acetic acid (0.029 mL, 0.504 mmol), and sodium cyanide (0.082 g, 1.679 mmol) in 4 mL THF was stirred rapidly overnight. Manganese dioxide (0.584 g, 6.72 mmol) was added, the reaction was sealed, and stirred rapidly for 3 days. The reaction was filtered through Celite® (diatomaceous earth), rinsing with 10% MeOH/DCM. The residue was adsorbed onto 2 g silica gel, dried, and purified by silica gel chromatography (40 g column) using 0-100% EtOAc/hexane. The product-containing fractions were concentrated to afford methyl 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)nicotinate (0.107 g, 0.171 mmol, 50.9% yield) as a orange solid. m/z (ESI, +ve ion) 626 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 12.33 (br. s., 1H), 9.41 (d, J=2.3 Hz, 1H), 8.92 (d, J=2.3 Hz, 1H), 7.98 (d, J=2.3 Hz, 1H,) 7.90-7.97 (m, 1H), 7.16-7.25 (m, 4H), 6.82-6.92 (m, 4H), 4.90 (s, 2H), 4.84 (s, 2H,) 4.04 (s, 3H), 3.92 (s, 3H), 3.82 (s, 3H), 3.79 (s, 3H), 2.61 (s, 3H).

Provenance & Evidence