Réaction #702135

Équation de réaction

Diacetylguanine

acetic anhydride

p-toluenesulfonic acid

dioxolane

→

9-(2-hydroxyethoxymethyl)guanine

Rendement 21.6%

Solvants

toluene

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source