Phosphoric Acid → HCID 25118843, compound

Participants

Reaction Steps

1,3,5-Tris[(6-amino-pyridin-2-yl)aminomethyl]-2,4,6-trimethylbenzene (2a) (2.0 g, 4.1 mmol), 4,4-dimethoxy-2-butanone (12.3 mmol), and H3PO4 (50 mL) were held at 90° for 4 h and then stirred at room temperature for 2 h. The reaction mixture was poured into water (200 mL), neutralized, and extracted several times with chloroform. The collected organic layers were dried over MgSO4 and the solvent was removed under reduced pressure. The crude product was purified several times by column chromatography (silica gel, CHCl3/CH3OH, 7:1 to 2:1 v/v). Yield 30%. M.p. 207-208° C. 1H-NMR (400 MHz, CDCl3): δ=2.34 (s, 9H), 2.61 (s, 9H), 4.71 (d, 6H, 3H, J=3.0 Hz), 5.12 (t, 3H, J=3.0 Hz), 6.60 (d, 3H, J=8.8 Hz), 6.98 (d, 3H, J=8.0 Hz), 7.65 (d, 3H, J=8.8 Hz), 7.74 (d, 3H, J=8.0 Hz). 13C NMR (100 MHz, CDCl3): δ=15.9, 25.0, 41.1, 112.4, 114.9, 115.9, 133.3, 136.0, 136.5, 137.2, 156.5, 158.7, 161.3. HR-MS calcd for C39H38N9: 632.3250; found: 632.3256. Rf=0.80 (CHCl3/CH3OH 2:1 v/v).

Provenance & Evidence