Reaktion #5963

Reaktionsgleichung

9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine

ammonium formate

→

2-Amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturunder reflux for 40 minutes
3. 3
   TemperaturAfter cooling the solution
4. 4
   Filtrationwas filtered
5. 5
   Sonstigethe solvent removed
6. 6
   Extraktionextracted with chloroform (100 ml and 50 ml)
7. 7
   Trocknendried (magnesium sulphate)
8. 8
   Sonstigethe solvent removed
9. 9
   workup.DISSOLUTIONThe residue was dissolved in methanol saturated with ammonia at 0° C. (150 ml)
10. 10
    SonstigeThe solvent was removed
11. 11
    Filtrationfiltered
12. 12
    SonstigeThe solid was recrystallised from isopropanol-water
13. 13
    Sonstigea second recrystallisation

Vorschrift

To a suspension of 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine (4.86 g, 13.7 mmol) in methanol (140 ml) containing ammonium formate (400 mM) was added 10% palladium-on-charcoal (0.4 g) and the mixture was heated under reflux for 40 minutes. After cooling the solution was filtered and the solvent removed. The residue was taken up in water and extracted with chloroform (100 ml and 50 ml). The organic layers were combined, dried (magnesium sulphate) and the solvent removed. The residue was dissolved in methanol saturated with ammonia at 0° C. (150 ml) and the solution was stirred for 20 hours. The solvent was removed and the residue suspended in chloroform (20 ml) and filtered. The solid was recrystallised from isopropanol-water and a second recrystallisation was carried out from the mother liquors from ethanol (total 2.71 g, 83%).

Quelle