Reaction #489502

Reaction equation

AICAR

sodium nitrite

ammonia

→

title compound

7-(β-D-Ribofuranosyl)imidazo[4,5-d]-v-triazin-4-one

Solvents

ethanol

Conditions

Workup

1. 1
   OtherSynthesis, 2003
2. 2
   workup.ADDITIONNo 17, 2639] (1 g, 3.87 mmol) was added to a solution of chlorhydrique acid 6N (25 mL) at −30° C
3. 3
   workup.ADDITIONwas added
4. 4
   OtherThe reaction mixture was evaporated to dryness
5. 5
   OtherThe crude product was purified on silica gel reverse-phase (C18)

Procedure

The AICAR [for preparation see Synthesis, 2003. No 17, 2639] (1 g, 3.87 mmol) was added to a solution of chlorhydrique acid 6N (25 mL) at −30° C. A solution of sodium nitrite 3M (4 ml, 11.62 mmol) was added and the mixture was stirred at −30° for 2 hours. A pre-cooled (−30° C.) solution of ethanol (25 mL) was added. A solution of ammonia (28%) was added at −20° C. to pH=7. The reaction mixture was evaporated to dryness. The crude product was purified on silica gel reverse-phase (C18) using water as eluant to give the title compound (0.81 gr) as a white powder.

Source