Reaction #1483053

Reaction equation

sodium nitrite

HCl

ethyl 3-hydroxypropanimidate hydrochloride

2-Pyrimidinecarbonitrile

hydrazine hydrate

→

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

Solvents

water

Conditions

Workup

1. 1
   Temperaturethe mixture was cooled
2. 2
   Filtrationfiltered
3. 3
   workup.STIRRINGwith stirring
4. 4
   OtherThe solution was dried by rotary evaporation
5. 5
   Washthe residue was washed with methanol (2×10 mL)
6. 6
   Filtrationfiltered
7. 7
   Otherthe filtrate was dried by rotary evaporation

Procedure

To a mixture of ethyl 3-hydroxypropanimidate hydrochloride (1 mmol, 153 mg) and 2-Pyrimidinecarbonitrile (5 mmol, 525 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-(pyrimidin-2-yl)-1,2,4,5-tetrazin-3-yl)ethanol (26 mg, 12.7%), as a pink solid. LRMS-ESI [M+H]+ calcd. for C8H9N6O+: 205.08, found: 204.9.

Source