Réaction #5962

Équation de réaction

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

ammonium formate

→

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

Rendement 90.2%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureunder reflux for 30 minutes
3. 3
   Températureto cool
4. 4
   Filtrationfiltered
5. 5
   Autrethe solvent removed
6. 6
   Extractionthe solution extracted twice with chloroform
7. 7
   Séchagedried (magnesium sulphate)
8. 8
   Autrethe solvent removed

Mode opératoire

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%).

Source