反应 #1596984

反应方程式

Compound 40

7-Allyl-2-amino-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-7,9-dihydro-1H-purine-6,8-dione

phosphorus oxychloride

→

desired product 41

收率 41.0%

7-Allyl-2-amino-6-chloro-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-7,9-dihydro-purin-8-one

收率 41.0%

反应条件

后处理

1. 1
   浓缩The reaction mixture was concentrated under vacuum
2. 2
   workup.DISSOLUTIONthe crude product dissolved in DCM
3. 3
   洗涤The mixture was then washed with NaHCO3 solution, brine
4. 4
   干燥dried (MgSO4)
5. 5
   过滤filtered
6. 6
   浓缩The filtrate was concentrated under vacuum
7. 7
   其他purified by flash chromatography
8. 8
   其他Removal of the solvent

实验过程

Compound 40 (0.65 g, 1.39 mmol) was dissolved in phosphorus oxychloride (10 mL) and heated to 75° C. for 16 h. The reaction mixture was concentrated under vacuum and the crude product dissolved in DCM. The mixture was then washed with NaHCO3 solution, brine, dried (MgSO4) and filtered. The filtrate was concentrated under vacuum and purified by flash chromatography using 10 to 50% gradient of ethyl acetate in hexanes. Removal of the solvent afforded 280 mg (41%) of the desired product 41: 1H NMR (400 MHz, CDCl3) δ 6.04 (d, J=4.0 Hz, 1H), 6.03 (t, J=5.6 Hz, 1H), 5.87 (m, 1H), 5.86 (t, J=5.6 Hz, 1H), 5.18 (m, 4H), 4.59 (d, J=8.0 Hz, 2H), 4.45 (d, J=7.6 Hz, 1H), 4.31 (m, 2H), 2.10 (s, 3H), 2.08 (s, 3H), 2.04 (s, 3H); MS (+)-ES [M+H]+ 484.2 m/z.

来源