HCID 66611452, compound → HCID 59548264, compound

Participants

Reaction Steps

A solution of 4-(2-(5-chloro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.3068 g, 0.525 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature, and 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 solid was dissolved in DCM and MeOH, and dry packed with silica gel. Purification using an ISCO Combiflash Companion (12 g column, 1-6% MeOH in DCM over 40 min, product eluted with 4% MeOH) gave 4-(2-(5-chloro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.0434 g, 0.126 mmol, 24.03% yield) as a tan amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.89 (s, 1H); 8.80 (dd, J=7.8, 2.0 Hz, 1H); 8.51-8.56 (m, 2H); 8.35 (dd, J=4.7, 2.0 Hz, 1H); 7.92 (br. s., 1H); 7.76 (br. s., 1H); 6.94 (dd, J=7.8, 4.7 Hz, 1H); 3.93 (s, 3H); 2.43 (s, 3H). m/z (ESI, +ve ion) 344.0 (M+H)+.

Provenance & Evidence