Reaction #1596984

Reaction equation

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

Yield 41.0%

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

Yield 41.0%

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated under vacuum
2. 2
   workup.DISSOLUTIONthe crude product dissolved in DCM
3. 3
   WashThe mixture was then washed with NaHCO3 solution, brine
4. 4
   Dryingdried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   ConcentrationThe filtrate was concentrated under vacuum
7. 7
   Otherpurified by flash chromatography
8. 8
   OtherRemoval of the solvent

Procedure

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.

Source