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

Participants

Reaction Conditions

Reaction Steps

A suspension of N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-((1-(methylsulfonyl)piperidin-4-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.1923 g, 0.265 mmol) in TFA (1.022 mL, 13.26 mmol) was treated with a couple of drops of methanesulfonic acid (0.017 mL, 0.265 mmol) and the yellow solution was heated at 80° C. overnight. The volatile material was removed and the residue was carefully diluted with 5% 2 M NH3 in MeOH/DCM. The solution was concentrated with SiO2 and chromatographed through a Redi-Sep pre-packed silica gel column (pure DCM→10% MeOH in DCM w/NH3). Following concentration of the eluent, the resulting yellow solid was washed with IPA to give 4-(2-(6-methoxypyridin-3-ylamino)-5-((1-(methylsulfonyl)piperidin-4-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (88 mg, 0.182 mmol, 68.5% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.66 (s, 1H); 8.60 (d, J=2.54 Hz, 1H); 8.54 (d, J=2.54 Hz, 1H); 8.17 (dd, J=8.90, 2.64 Hz, 1H); 8.14 (d, J=2.15 Hz, 1H); 7.84 (br. s., 1H); 7.71 (br. s., 1H); 6.81 (d, J=8.80 Hz, 1H); 3.84 (s, 3H); 3.45-3.62 (m, 2H); 2.82 (s, 3H); 2.61-2.72 (m, 2H); 2.43 (s, 3H); 1.67-1.68 (m, 2H); 1.46-1.64 (m, 1H); 1.15-1.32 (m, 2H). m/z (ESI, +ve ion) 485.2 (M+H)+.

Provenance & Evidence