N#N.[CH3:3][O:4][C:5]1[N:6]=[CH:7][N:8]=[N:9][C:10]=1[CH2:11][NH2:12].[O:13]=[C:14]1[CH2:17][CH:16]([C:18](ON2C(=O)CCC2=O)=[O:19])[CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+]>O.[Cl-].[Na+].O.C1COCC1>[CH3:3][O:4][C:5]1[N:6]=[CH:7][N:8]=[N:9][C:10]=1[CH2:11][NH:12][C:18]([CH:16]1[CH2:17][C:14](=[O:13])[CH2:15]1)=[O:19]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).
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