HCID 66611824, compound → HCID 59548190, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-(thiomorpholinomethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (86 mg, 0.129 mmol) in 2 mL of TFA was treated with 2 drops of triflic acid. The brown solution was heated in an oil bath at 80° C. for 5 h. The volatiles were removed on and the dark residue was basified with 1 N NaOH and extracted with EtOAc twice followed by DCM once. The combined organic extracts were concentrated and purified on a Redi-Sep pre-packed silica gel column (12 g) eluting with a gradient of 2-6% MeOH in DCM to give 4-(2-(6-methoxypyridin-3-ylamino)-5-(thiomorpholinomethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (30 mg, 55% yield) as an orange crystalline solid. 1H NMR (400 MHz, d6-DMSO) δ 11.75 (1H, s); 8.68 (1H, d, J=2.4Hz); 8.54 (1H, d, J=2.7 Hz); 8.18 (1H, d, J=2.5 Hz); 8.16 (1H, d J=2.9 Hz); 7.87 (1H, br. s); 7.73 (1H, br. s); 6.82 (1H, d, J=9.0 Hz); 3.84 (3H, s); 3.46 (2H, s); 2.67-2.60 (8H, m); 2.44 (3H, s). m/z (ESI, +ve ion) 425 (M+H)+.

Provenance & Evidence