[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([CH:9]=O)=O)[CH:2]=1.C(=O)(O)O.[NH2:15][NH:16][C:17]([NH2:19])=[NH:18]>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:18]=[C:17]([NH2:19])[N:16]=[N:15][CH:9]=2)[CH:2]=15-(Pyridin-3-yl)-1,2,4-triazin-3-amine (1.5 g, 16% over 2 steps) was prepared from a crude sample of 3-pyridylglyoxal (10.0 g) and aminoguanidine hydrogen carbonate (3.0 g, 22 mmol). The reagents were refluxed in EtOH (100 mL) for 4 hours. The reaction mixture was then cooled, concentrated under reduced pressure and purified by gradient flash chromatography (eluting with 0-30% ethyl acetate/hexane).
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