3-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)-N-(6-methoxypyridin-3-YL)quinolin-2-amine → 3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxypyridin-3-yl)quinolin-2-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxypyridin-3-yl)quinolin-2-amine (0.16 g, 0.26 mmol) in TFA (3 mL) was treated with a couple of drops of trifluoromethane sulfonic acid. The reaction mixture was stirred at 90° C. for 18 h, allowed to cool to room temperature, and the solvent was removed in vacuo. Purification by reverse-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 90% over 18 min gave 3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxypyridin-3-yl)quinolin-2-amine (31 mg, 0.09 mmol, 33% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.99 (br. s., 1H); 9.33 (s, 1H); 8.88 (br. s., 1H); 8.42 (d, J=7.43 Hz, 1H); 7.77-8.09 (m, 3H); 7.67 (br. s., 2H); 7.33 (br. s., 1H); 6.87 (d, J=8.80 Hz, 1H); 3.87 (s, 3H); 2.49 (s, 3H). m/z (ESI, +ve ion) 359.9 (M+H)+.

Provenance & Evidence