HCID 66611145, compound → HCID 59548406, compound

Participants

Reaction Conditions

Reaction Steps

A few drops of triflic acid were added to a solution of 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-3-morpholinone (0.115 g, 0.174 mmol) in 2 mL of TFA at RT. The mixture was heated to 80° C. for 1 h. The reaction was cooled and concentrated, but not to dryness. A few ice cubes were added and saturated NaHCO3 (aq.) was added until pH=7. The yellow solid was filtered washed with water, CH2Cl2, MeOH and Et2O and collected and dried under vacuum. The aqueous layer was extracted with 3/1 CHCl3/n-BuOH (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude material was adsorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (4 g), eluting with a gradient of 0% to 10% MeOH in CH2Cl2. This material was combined with the yellow solid collected above to provide 4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-3-morpholinone (0.040 g, 0.095 mmol, 54.6% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.76 (s, 1H); 8.70 (dd, J=2.15, 0.39 Hz, 1H); 8.53 (dd, J=2.54, 0.39 Hz, 1H); 8.24 (dd, J=2.05, 0.49 Hz, 1H); 8.13-8.19 (m, 1H); 7.88 (br. s., 1H); 7.72 (br. s., 1H); 6.82 (d, J=8.80 Hz, 1H); 4.52 (s, 2H); 4.10 (s, 2H); 3.84 (s, 3H); 3.79-3.83 (m, 2H); 3.27-3.32 (m, 2H); 2.43 (s, 3H). m/z (ESI, +ve ion) 423.2 (M+H)+.

Provenance & Evidence