Morpholine → HCID 66600185, compound

Participants

Reaction Steps

A solution of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinecarbaldehyde (0.127 g, 0.220 mmol) in THF (2.00 mL) was treated with sodium cyanide (10.77 mg, 0.220 mmol), morpholine (0.096 mL, 1.099 mmol) and manganese (IV) oxide (0.287 g, 3.30 mmol) at ambient temperature. After 30 min, more manganese (IV) oxide (0.287 g, 3.30 mmol) was added and the mixture was stirred overnight at ambient temperature. The mixture was filtered through Celite® (diatomaceous earth) and the organic layer was washed with water followed by saturated NaCl (aq.) and then dried over anhydrous Na2SO4, filtered and concentrated to give N,N-bis(4-methoxybenzyl)-4-(2-((6-methoxy-3-pyridinyl)amino)-5-(4-morpholinylcarbonyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine (0.128 g, 0.193 mmol, 88% yield) as a brown foam. 1H NMR (400 MHz, CDCl3) δ 11.95 (s, 1H); 8.90 (d, J=2.54 Hz, 1H); 8.39 (d, J=2.35 Hz, 1H); 8.28 (d, J=2.74 Hz, 1H); 7.89 (dd, J=8.80, 2.74 Hz, 1H); 7.13-7.24 (m, 4H); 6.81-6.90 (m, 4H); 6.73 (d, J=8.80 Hz, 1H); 4.85 (s, 2H); 4.82 (s, 2H); 3.94 (s, 3H); 3.81 (s, 3H); 3.78 (s, 3H); 3.57-3.69 (m, 8H); 2.59 (s, 3H). m/z (ESI, +ve ion) 663.2 (M+H)+.

Provenance & Evidence