N,N-Bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)phenyl)-6-methyl-1,3,5-triazin-2-amine → 4-(2-(6-Methoxypyridin-3-ylamino)phenyl)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

A solution of N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)phenyl)-6-methyl-1,3,5-triazin-2-amine (0.38 g, 0.70 mmol) in TFA (3 mL) was treated with several drops of trifluoromethane sulfonic acid and heated at 80° C. for 3 h. The solvent was removed in vacuo and the residue was purified by reverse phase preparative HPLC using a Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in MeCN/H2O gradient to give 4-(2-(6-methoxypyridin-3-ylamino)phenyl)-6-methyl-1,3,5-triazin-2-amine (47 mg, 0.15 mmol, 22% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 10.92 (s, 1H); 8.44 (dd, J=8.12, 1.66 Hz, 1H); 8.12 (d, J=2.74 Hz, 1H); 7.68 (dd, J=8.80, 2.74 Hz, 2H); 7.53 (br. s., 1H); 7.28 (ddd, J=8.46, 6.99, 1.57 Hz, 1H); 6.88 (dd, J=12.81, 8.51 Hz, 2H); 6.69-6.82 (m, 1H); 3.86 (s, 3H); 2.38 (s, 3H). m/z (ESI, +ve ion) 309.0 (M+H)+.

Provenance & Evidence