6-Methoxy-3-pyridinylamine → 5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)-N-(6-methoxypyridin-3-YL)-2,3'-bipyridin-6-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(6-fluoro-2,3′-bipyridin-5-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (230 mg, 0.440 mmol) and 5-amino-2-methoxypyridine (0.082 mL, 0.660 mmol) (Aldrich) in THF (6.0 mL) was cooled to 0° C. in an ice bath and treated with 1 M LiHMDS (1.320 mL, 1.320 mmol) (Aldrich) resulting in a deep purple solution which was stirred at 0° C. for 30 min. The reaction was quenched by the addition of a saturated solution of NH4Cl and extracted with EtOAc (20 mL), washed with brine and dried over MgSO4, filtered and concentrated. The crude material was used in the next step without further purification. m/z (ESI, +ve ion) 627.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 11.89 (1H, s); 9.25 (1H, d, J=1.6 Hz); 8.91 (1H, d, J=8.2 Hz); 8.64 (1H, dd, J=4.8, 1.7 Hz); 8.37 (1H, d, J=2.5 Hz); 8.31 (1H, dt, J=8.0, 2.0 Hz); 8.01 (1H, dd, J=8.9, 2.6 Hz); 7.66 (1H, d, J=2.7 Hz); 7.39 (1H, dd, J=7.8, 4.7 Hz); 7.18-7.25 (4H, m); 7.03 (1H, dd, J=8.6, 2.9 Hz); 6.82-6.91 (4H, m); 4.85 (4H, s); 3.86 (3H, s); 3.81 (3H, s); 3.79 (3H, s); 2.60 (3H, s).

Provenance & Evidence