반응 #5962

반응 방정식

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

ammonium formate

→

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

수율 90.2%

용매

methanol

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux for 30 minutes
3. 3
   온도to cool
4. 4
   여과filtered
5. 5
   기타the solvent removed
6. 6
   추출the solution extracted twice with chloroform
7. 7
   건조dried (magnesium sulphate)
8. 8
   기타the solvent removed

실험 절차

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%).

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