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

Participants

Reaction Steps

A stirred solution of N5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl)pyridine-2,5-diamine (Example 190, Step 4, 0.124 g, 0.233 mmol) in THF (2 mL) was treated with 2-isocyanatopropane (Aldrich) (0.046 mL, 0.465 mmol) and the yellow solution was stirred at rt overnight. The mixture was concentrated and the crude product was purified by silica gel chromatography (25 g, eluent: iPrOH (w/10% NH4OH) in CHCl3 0%-7.5%) 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-isopropylurea (0.1044 g, 72% yield) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 11.74 (s, 1H); 8.98-9.14 (m, 1H); 8.83 (d, J=7.75 Hz, 1H); 8.35 (d, J=1.75 Hz, 1H); 8.24-8.33 (m, 1H); 7.84 (dd, J=8.77, 1.90 Hz, 1H); 7.35 (s, 1H); 7.20 (t, J=8.33 Hz, 4H); 6.86 (t, J=7.38 Hz, 4H); 6.77 (dd, J=7.75, 4.82 Hz, 1H); 6.65 (d, J=8.77 Hz, 1H); 4.84 (d, J=4.97 Hz, 4H); 4.01-4.18 (m, 1H); 3.80 (d, J=7.31 Hz, 6H); 2.60 (s, 3H); 1.28 (d, J=6.58 Hz, 6H). m/z (ESI, +ve ion) 620.0 (M+H)+.

Provenance & Evidence