Hydrochloric Acid → 2-(6-Methyl-1,2,4,5-tetrazin-3-yl)ethanol
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Cl.[OH:2][CH2:3][CH2:4][C:5](=[NH:9])OCC.Cl.[C:11]([NH2:14])(=[NH:13])[CH3:12].O.NN.[N:18]([O-])=O.[Na+].Cl>O>[CH3:12][C:11]1[N:14]=[N:9][C:5]([CH2:4][CH2:3][OH:2])=[N:18][N:13]=1Cl.[OH:2][CH2:3][CH2:4][C:5](=[NH:9])OCC.Cl.[C:11]([NH2:14])(=[NH:13])[CH3:12].O.NN.[N:18]([O-])=O.[Na+].Cl>O>[CH3:12][C:11]1[N:14]=[N:9][C:5]([CH2:4][CH2:3][OH:2])=[N:18][N:13]=1
To a mixture of ethyl 3-hydroxypropanimidate hydrochloride (2 mmol, 307 mg) and acetamidine hydrochloride (10 mmol, 945 mg) was added hydrazine hydrate (2 mL) under an atmosphere of argon. After stirring at room temperature for 2 hours, the mixture was diluted with water (25 mL) and sodium nitrite (25 mmol, 1.72 g) was added. To this solution was added 2% aqueous HCl dropwise on an ice bath until the now pink solution reached a pH of 3. The aqueous solution was extracted with methylene chloride (5×50 mL), dried with magnesium sulfate, the solvent was removed by rotary evaporation, and then dried under vacuum to afford the product, 2-(6-methyl-1,2,4,5-tetrazin-3-yl)ethanol (140 mg, 37%), as a pink oil. LRMS-ESI [M+H]+ calcd. for C5H9N4O+: 141.08, found: 140.7.
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