HCID 66611199, compound → HCID 59548210, compound

Participants

Reaction Steps

A solution of 4-(2-(3,4-dimethoxyphenylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.255 g, 0.441 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature, the mixture was concentrated, the crude residue was treated with 2M NH3 in MeOH and dry-packed with silica gel. Purification using an ISCO Combiflash Companion (12 g column; 1-25% MeOH in DCM over 30 min; product eluted with 11% MeOH) gave material of insufficient purity for testing. The residue was suspended in MeOH and the solid was removed by filtration to give 4-(2-(3,4-dimethoxyphenylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.017 g, 0.049 mmol, 11.12% yield) as a brown amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.77 (s, 1H); 8.75 (dd, J=7.7, 1.9 Hz, 1H); 8.31 (dd, J=4.5, 2.0 Hz, 1H); 7.79 (br. s., 1H); 7.70 (br. s., 1H); 7.47 (d, J=2.3 Hz, 1H); 7.30 (dd, J=8.7, 2.4 Hz, 1H); 6.91 (d, J=8.8 Hz, 1H); 6.84 (dd, J=7.8, 4.7 Hz, 1H); 3.79 (s, 3H); 3.74 (s, 3H); 2.44 (s, 3H). m/z (ESI, +ve ion) 339.0 (M+H)+.

Provenance & Evidence