반응 #1596984

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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

수율 41.0%

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

수율 41.0%

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated under vacuum
2. 2
   workup.DISSOLUTIONthe crude product dissolved in DCM
3. 3
   세척The mixture was then washed with NaHCO3 solution, brine
4. 4
   건조dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축The filtrate was concentrated under vacuum
7. 7
   기타purified by flash chromatography
8. 8
   기타Removal of the solvent

실험 절차

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.

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