Nitrogen → N-[(5-methoxy-1,2,4-triazin-6-yl)methyl]-3-oxocyclobutanecarboxamide

Participants

Reaction Steps

A flask filled with N2 was charged with 1-(5-methoxy-1,2,4-triazin-6-yl)methylamine (3.0 g, 0.021 mol), 1-{[(3-oxocyclobutyl)carbonyl]oxy}pyrrolidine-2,5-dione (5.0 g, 0.024 mol) and THF (50 mL). Sodium carbonate (20 g, 0.2 mol) dissolved in water was added to the reaction mixture slowly at 0° C. The reaction was then stirred at rt for 3 h. The reaction mixture was then concentrated under reduced pressure to give a residue. To this residue brine (500 mL) was added and the mixture was extracted with EtOAc (100 mL×3). The organics were combined, dried (Na2SO4) and concentrated under reduced pressure to give a crude residue, which was then purified by flash chromatography on silica gel using hexanes:EtOAc (2:1) as the eluent. 1H NMR (400 MHz, Chloroform-d) δ 3.12-3.33 (m, 3H), 3.44-3.58 (m, 2H), 4.11 (s, 3H), 4.75 (d, J=4.80 Hz, 2H), 7.11 (br. s., 1H), 9.08 (s, 1H).

Provenance & Evidence