Reaktion #5962

Reaktionsgleichung

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

ammonium formate

→

9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-aminopurine

Ausbeute 90.2%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 30 minutes
3. 3
   Temperaturto cool
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe solvent removed
6. 6
   Extraktionthe solution extracted twice with chloroform
7. 7
   Trocknendried (magnesium sulphate)
8. 8
   Sonstigethe solvent removed

Vorschrift

A suspension of 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine (0.36 g, 1.0 mmol) and 10% palladium-on-charcoal (30 mg) in methanol containing ammonium formate (400 mM, 10 ml) was heated under reflux for 30 minutes. The mixture was allowed to cool, filtered and the solvent removed. The residue was taken up in water and the solution extracted twice with chloroform. The organic layers were combined, dried (magnesium sulphate) and the solvent removed to afford 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-aminopurine (0.29 g, 90%). Recrystallisation from ethyl acetate-hexane gave white shiny plates (0.25 g, 78%) m.p. 102°-104° C.; λmax (MeOH) 222 (27,500), 244 (4,890), and 309 (7,160) nm; νmax (KBr) 3340, 3170, 1745, 1730, 1660, 1615 and 1580 cm-1 ; δH (CDCl3) 1.90-2.05 (3H, m, 2'-H and 3' -H), 2.07 (6H, s, 2×CH3), 4.15 (4H, d, J 5.2 Hz, 2×4'-H), 4.21 (2H, t, J 7.2 Hz, 1'-H), 5.16 (2H, br s, 2-NH2), 7.79 (1H, s, 8-H), and 8.70 (1H, s, 6-H); (Found: C, 52.10; H, 6.00; N, 21.49%. C14H19N5O4 requires C, 52.33; H, 5.96; N, 21.79%).

Quelle