N,N-Bis(4-methoxybenzyl)-4-methyl-6-(2-(5-methylpyridin-3-ylamino)pyridin-3-YL)-1,3,5-triazin-2-amine → 4-Methyl-6-(2-(5-methylpyridin-3-ylamino)pyridin-3-yl)-1,3,5-triazin-2-amine

Participants

Reaction Steps

A solution of N,N-bis(4-methoxybenzyl)-4-methyl-6-(2-(5-methylpyridin-3-ylamino)pyridin-3-yl)-1,3,5-triazin-2-amine (0.063 g, 0.118 mmol) in TFA (3.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature and was concentrated to about 50% of the original volume. The remaining mixture was pipetted carefully into a saturated solution of NaHCO3, which had been cooled in an ice bath. The resulting precipitate was removed by filtration and washed with water. The material was suspended in DMSO (5 mL) and water (10 drops) was added. The solid was collected by filtration to give 4-methyl-6-(2-(5-methylpyridin-3-ylamino)pyridin-3-yl)-1,3,5-triazin-2-amine (0.0137 g, 0.047 mmol, 39.6% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.96-12.04 (m, 1H); 8.81 (br. s., 2H); 8.39 (br. s., 1H); 8.23 (br. s., 1H); 8.05 (s, 1H); 7.89 (br. s., 1H); 7.77 (br. s., 1H); 6.96 (br. s., 1H); 2.45 (br. s., 3H); 2.32 (s, 3H). m/z (ESI, +ve ion) 294.0 (M+H)+.

Provenance & Evidence