Trifluoromethanesulfonic acid → 4-(3-(6-Methoxypyridin-3-ylamino)pyridin-4-yl)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Steps

A glass microwave reaction vessel was charged with N,N-bis(4-methoxybenzyl)-4-(3-(6-methoxypyridin-3-ylamino)pyridin-4-yl)-6-methyl-1,3,5-triazin-2-amine (7 mg, 0.013 mmol) and trifluoromethane sulfonic acid (3.38 μL, 0.038 mmol) in TFA (0.1 mL). The reaction mixture was stirred and heated in an oil bath at room temperature for 2 h. The reaction mixture was diluted with saturated NaHCO3 (5 mL) and extracted with EtOAc (2×20 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow solid. The crude product was purified by silica gel chromatography eluting with EtOAc to give 4-(3-(6-methoxypyridin-3-ylamino)pyridin-4-yl)-6-methyl-1,3,5-triazin-2-amine (3.2 mg, 10.35 μmol, 81% yield). 1H NMR (300 MHz, CDCl3) δ 10.38 (s, 1H); 8.38 (s, 1H); 8.24 (d, J=5.12 Hz, 1H); 8.13 (s, 1H); 8.07 (d, J=4.97 Hz, 1H); 7.58 (dd, J=8.77, 2.05 Hz, 1H); 6.81 (d, J=8.77 Hz, 1H); 5.41 (s, 2H); 3.96 (s, 3H); 2.54 (s, 3H). m/z (ESI, +ve ion) 310.0 (M+H)+.

Provenance & Evidence