Reacción #1483052

Ecuación de reacción

sodium nitrite

HCl

ethyl 3-hydroxypropanimidate hydrochloride

2-pyridinecarbonitrile

hydrazine hydrate

→

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

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was cooled
2. 2
   Filtraciónfiltered
3. 3
   workup.STIRRINGwith stirring
4. 4
   OtroThe solution was dried by rotary evaporation
5. 5
   Lavadothe residue was washed with methanol (2×10 mL)
6. 6
   Filtraciónfiltered
7. 7
   Otrothe filtrate was dried by rotary evaporation

Procedimiento

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.

Fuente