Réaction #1483052

Équation de réaction

sodium nitrite

HCl

ethyl 3-hydroxypropanimidate hydrochloride

2-pyridinecarbonitrile

hydrazine hydrate

→

2-(6-(Pyridin-2-yl)-1,2,4,5-tetrazin-3-yl)ethanol

Solvants

water

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was cooled
2. 2
   Filtrationfiltered
3. 3
   workup.STIRRINGwith stirring
4. 4
   AutreThe solution was dried by rotary evaporation
5. 5
   Lavagethe residue was washed with methanol (2×10 mL)
6. 6
   Filtrationfiltered
7. 7
   Autrethe filtrate was dried by rotary evaporation

Mode opératoire

To 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.

Source