2,6-Diaminopyridine → HCID 11203277, compound

Participants

Reaction Steps

A mixture of 1,3,5-tris(bromomethyl)-2,4,6-triethyl-benzene (0.79 g, 1.8 mmol), 2,6-diamino-pyridine (1.20 g, 11 mmol), and K2CO3 (0.79 g) in CH3CN (100 mL) was stirred at room temperature for 24 h and then heated under reflux for 2 h. After filtration of the reaction mixture and evaporation of CH3CN, the obtained powder was suspended in CHCl3. The suspension was filtrated, the chloroform solution was washed several times with water, dried, and the solvent was removed under reduced pressure. The crude product was crystallized from THF/hexane. Yield 40%. M.p. 164-165° C.; 1H NMR (500 MHz, CDCl3): δ=1.22 (t, 9H, J=7.5 Hz), 2.75 (q, 6H, J=7.5 Hz), 4.05 (t, 3H, J=4.2 Hz), 4.20 (s, 6H), 4.35 (d, 6H, J=4.2 Hz), 5.83-5.86 (m, 6H), 7.24 (m, 3H); 13C NMR (125 MHz, CDCl3): δ=16.9, 23.0, 40.6, 95.9, 96.9, 133.3, 139.4, 143.8, 157.8, 157.9; HR-MS calcd for C30H39N9: 525.3328; found: 525.3322. Rf=0.21 (CHCl3/CH3OH 7:1 v/v).

Provenance & Evidence