Reacción #702135

Ecuación de reacción

Diacetylguanine

acetic anhydride

p-toluenesulfonic acid

dioxolane

→

9-(2-hydroxyethoxymethyl)guanine

Rendimiento 21.6%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool for several minutes
2. 2
   Temperaturaat reflux for 18 hr
3. 3
   OtroThe toluene was decanted off
4. 4
   Otrothe residue triturated several times with benzene
5. 5
   workup.ADDITIONMethanol (10 ml) was added to the residue
6. 6
   Otroevaporated under reduced pressure
7. 7
   workup.ADDITIONTo the residue was added 40% aqueous methylamine (10 ml)
8. 8
   Temperaturathe mixture heated on a steam bath for 20 min
9. 9
   OtroThe water and methylamine were removed under reduced pressure, ethanol (10 ml)
10. 10
    workup.ADDITIONwas added
11. 11
    Otroevaporated
12. 12
    ExtracciónThe residue was thoroughly extracted with boiling methanol (700 ml total)
13. 13
    Otrothe combined extracts evaporated
14. 14
    OtroThe resulting solid was triturated with cold ethanol
15. 15
    Otrorecrystallized from methanol

Procedimiento

To a mixture of acetic anhydride (1.2 ml) and p-toluenesulfonic acid (0.09 g) was added with stirring dioxolane (1.02 g) - caution, exothermic. The solution was allowed to cool for several minutes. Diacetylguanine (1.45 g) and dry toluene (9 ml) were added and the reaction mixture was stirred at reflux for 18 hr. and then allowed to cool to room temperature. The toluene was decanted off and the residue triturated several times with benzene. Methanol (10 ml) was added to the residue and evaporated under reduced pressure. To the residue was added 40% aqueous methylamine (10 ml) and the mixture heated on a steam bath for 20 min. The water and methylamine were removed under reduced pressure, ethanol (10 ml) was added and evaporated. The residue was thoroughly extracted with boiling methanol (700 ml total) and the combined extracts evaporated. The resulting solid was triturated with cold ethanol and then recrystallized from methanol to give 9-(2-hydroxyethoxymethyl)guanine (0.3 g).

Fuente