反応 #1596984

反応方程式

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

収率 41.0%

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

収率 41.0%

反応条件

後処理

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

実験手順

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.

出典