HCID 66611387, compound → 4-[6'-[(6-Methoxy-3-pyridinyl)amino][2,3'-bipyridin]-5'-yl]-6-methyl-1,3,5-triazin-2-amine

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Reaction Steps

A solution of 5′-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxypyridin-3-yl)-2,3′-bipyridin-6′-amine (0.0419 g, 0.067 mmol) in TFA (3.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature and concentrated. The crude residue was treated with 2M NH3 in MeOH and dry-packed with silica gel. Purification on an ISCO Combiflash Companion (12 g column, 1-15% MeOH in DCM over 25 min, product eluted with 10% MeOH)) gave 5′-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxypyridin-3-yl)-2,3′-bipyridin-6′-amine (0.0106 g, 0.027 mmol, 41.0% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.98 (s, 1H); 9.53 (d, J=2.5 Hz, 1H); 9.00 (d, J=2.5 Hz, 1H); 8.67 (d, J=5.3 Hz, 1H); 8.58 (d, J=2.7 Hz, 1H); 8.21 (dd, J=9.0, 2.9 Hz, 1H); 7.96 (t, J=7.8 Hz, 2H); 7.88 (td, J=7.6, 1.8 Hz, 1H); 7.76 (d, J=2.7 Hz, 1H); 7.33 (s, 1H); 6.86 (d, J=9.0 Hz, 1H); 3.86 (s, 3H); 2.47 (s, 3H). m/z (ESI, +ve ion) 387.0 (M+H)+.

Provenance & Evidence