Acetic Anhydride → 7-(2-Thienyl)-3-(2,3-di-O-acetyl-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

HRID 1662299Notes

Reaction equation

HRID 1662299 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([C@@H:15]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[CH2:16]3)[CH:13]=[N:14][C:7]=12.[C:26]([O:29]C(=O)C)(=[O:28])[CH3:27]>N1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([C@@H:15]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]3[O:29][C:26](=[O:28])[CH3:27])[CH:13]=[N:14][C:7]=12

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 674285847-(2-Thienyl)-3-(2-deoxy-3-O-acetyl-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 674282737-(2-Thienyl)-3-(2,3-di-O-acetyl-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridineYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Compound 9 (247 mg, 0.4 mmol) was azeotroped with pyridine, followed by addition of pyridine (4 ml) and acetic anhydride (75 μl, 0.8 mmol). After stirring at room temperature for 12 hours, the reaction mixture was partitioned between ethyl acetate and 5% aqueous NaHCO3, and the organic layer was washed with 5% aqueous NaHCO3. This organic layer was dried over anhydrous sodium sulfate, concentrated and azeotroped with toluene. The residue was then dissolved in methylene chloride (40 ml). To this reaction mixture, dichloroacetic acid (400 μl) was added at 0° C. and stirred for 15 minutes at 0° C. The reaction mixture was partitioned with 5% aqueous NaHCO3, and the organic layer was washed with 5% aqueous NaHCO3. After drying over anhydrous sodium sulfate, the organic layer was concentrated and purified on a silica gel column to give Compound 13 (125 mg, 87%).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and 5% aqueous NaHCO3
  2. washthe organic layer was washed with 5% aqueous NaHCO3
  3. dry with materialThis organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customazeotroped with toluene
  6. dissolutionThe residue was then dissolved in methylene chloride (40 ml)
  7. additionTo this reaction mixture, dichloroacetic acid (400 μl) was added at 0° C.
  8. stirringstirred for 15 minutes at 0° C
  9. customThe reaction mixture was partitioned with 5% aqueous NaHCO3
  10. washthe organic layer was washed with 5% aqueous NaHCO3
  11. dry with materialAfter drying over anhydrous sodium sulfate
  12. concentrationthe organic layer was concentrated
  13. custompurified on a silica gel column

Sources & evidence

ORD record
ord-8a68bad9bc05489db13c1f16b51f2ff3
Source dataset
uspto-grants-2011_10
Patent number
US08030478B2

Reaction notes

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