HCID 66611911, compound → 4-[6'-Methoxy-6-[(6-methoxy-3-pyridinyl)amino][3,3'-bipyridin]-5-yl]-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Steps

A solution of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6′-methoxy-N-(6-methoxypyridin-3-yl)-3,3′-bipyridin-6-amine (0.163 g, 0.249 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 (40 g column; 1-20% MeOH in DCM over 25 min; product eluted with 10% MeOH) afforded 5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6′-methoxy-N-(6-methoxypyridin-3-yl)-3,3′-bipyridin-6-amine (0.0572 g, 0.137 mmol, 55.2% yield) as an orange colored amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.81 (s, 1H); 8.98 (d, J=2.7 Hz, 1H); 8.62 (d, J=2.5 Hz, 1H); 8.56 (d, J=2.7 Hz, 1H); 8.47 (d, J=2.3 Hz, 1H); 8.20 (dd, J=8.8, 2.7 Hz, 1H); 8.00 (dd, J=8.6, 2.7 Hz, 1H); 7.90 (br. s., 1H); 7.76 (br. s., 1H); 6.94 (d, J=8.6 Hz, 1H); 6.85 (d, J=8.8 Hz, 1H); 3.90 (s, 3H); 3.86 (s, 3H); 2.46 (s, 3H). m/z (ESI, +ve ion) 417.0 (M+H)+.

Provenance & Evidence