Trifluoroacetic acid → 4-(5-(Difluoromethoxy)-2-(6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Steps

A solution of 4-(5-(difluoromethoxy)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.022 g, 0.036 mmol) in trifluoroacetic acid (Aldrich) (0.531 mL, 7.15 mmol) and trifluoromethane sulfonic acid (TCI) (3.16 μL, 0.036 mmol) was heated at 80° C. for 20 min. The reaction mixture was concentrated and the residue was first diluted with sat. NaHCO3 (8 mL) then extracted with CHCl3 (3×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (12 g, 10% to 20% acetone in hexanes) to give the product as a yellow solid (0.010 g). m/z (ESI, +ve ion) 376.0 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 11.65 (s, 1H); 8.67 (br. s., 1H); 8.35 (br. s., 1H); 8.20 (br. s., 1H); 8.09 (d, J=9.94 Hz, 1H); 6.79 (d, J=8.92 Hz, 1H); 6.11-6.75 (m, 1H); 5.41 (br. s., 2H); 3.95 (s, 3H); 2.58 (s, 3H).

Provenance & Evidence