反応 #5962

反応方程式

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

ammonium formate

→

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

収率 90.2%

溶媒

methanol

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度under reflux for 30 minutes
3. 3
   温度to cool
4. 4
   ろ過filtered
5. 5
   その他the solvent removed
6. 6
   抽出the solution extracted twice with chloroform
7. 7
   乾燥dried (magnesium sulphate)
8. 8
   その他the solvent removed

実験手順

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%).

出典