Cl.O[CH2:3][CH2:4][C:5](=[NH:9])OCC.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]#[N:17].[OH2:18].[NH2:19][NH2:20].N([O-])=O.[Na+].Cl>O>[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:17]=[N:9][C:5]([CH2:4][CH2:3][OH:18])=[N:20][N:19]=1To a mixture of ethyl 3-hydroxypropanimidate hydrochloride (1 mmol, 153 mg) and 2-pyridinecarbonitrile (5 mmol, 520 mg) was added hydrazine hydrate (1 mL). After stirring at 90° C. for 1 hour, the mixture was cooled, diluted with water (10 mL), filtered, and to the filtrate was added sodium nitrite (10 mmol, 0.69 g) with stirring. To this pink solution was added 2% aqueous HCl dropwise on an ice bath until the solution reached a pH of 3. The solution was dried by rotary evaporation, the residue was washed with methanol (2×10 mL), filtered, and the filtrate was dried by rotary evaporation. Column chromatography on silica gel eluting with 1.5% methanol in methylene chloride afforded pure 2-(6-(pyridin-2-yl)-1,2,4,5-tetrazin-3-yl)ethanol (44 mg, 22%), as a pink solid. LRMS-ESI [M+H]+ calcd. for C9H10N5O+: 204.09, found: 203.9.
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