Phenyl isocyanate → 1-(5-(3-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)pyridin-2-yl)-3-phenylurea

Participants

Reaction Steps

A solution of N5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl)pyridine-2,5-diamine (0.150 g, 0.281 mmol) and phenyl isocyanate (Fluka) (0.077 mL, 0.70 mmol) in THF (3 mL) was stirred at rt for 5 h. The resulting solid was collected by filtration to give 1-(5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)pyridin-2-yl)-3-phenylurea (0.0707 g) as a yellow solid. The filtrate and wash were concentrated and purified by silica gel chromatography (25 g, eluent: EtOAc in hexanes 0%-30%) to give a second batch of the product (0.0924 g). The total yield was 0.1631 g, 89%. 1H NMR (300 MHz, CDCl3) δ 11.83 (s, 1H); 11.66 (br. s., 1H); 8.80-8.89 (m, 1H); 8.41 (br. s., 1H); 8.27-8.36 (m, 1H); 7.88-7.99 (m, 1H); 7.62 (d, J=8.18 Hz, 2H); 7.31-7.41 (m, 3H); 7.15-7.24 (m, 4H); 7.03-7.12 (m, 1H); 6.75-6.93 (m, 5H); 6.64-6.73 (m, 1H); 4.85 (br. s., 4H); 3.79 (d, J=10.96 Hz, 6H); 2.61 (s, 3H). m/z (ESI, +ve ion) 654.0 (M+H)+.

Provenance & Evidence