Acetic Anhydride → 1-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one

HRID 1447002Notes

Reaction equation

HRID 1447002 reaction equation
[C@@H:1]1([N:10]2[C:18]3[CH:17]=[CH:16][NH:15][C:14](=[O:19])[C:13]=3[N:12]=[CH:11]2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].C(O[C:24](=[O:26])[CH3:25])(=O)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:2]([O:3][C@H:2]1[C@H:4]([O:5][C:4](=[O:5])[CH3:6])[C@@H:6]([CH2:8][O:9][C:24](=[O:26])[CH3:25])[O:7][C@H:1]1[N:10]1[C:18]2[CH:17]=[CH:16][NH:15][C:14](=[O:19])[C:13]=2[N:12]=[CH:11]1)(=[O:3])[CH3:1]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 127994161-beta-D-arabinofuranosyl-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one

Product 1

HCID 540048091-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 3.0 g of 1-β-D-arabinofuranosyl-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one, eight ml of acetic anhydride, 150 ml of pyridine, and 50 mg of p-dimethylaminopyridine is stirred at room temperature for 24 hours, evaporated in vacuo, co-evaporated with xylenes, and distributed between water and ethyl acetate. The ethyl acetate layer is washed with saturated NaHCO3 and dried with MgSO4. Removal of the ethyl acetate provides 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one. This is dissolved in 150 ml of dry pyridine, treated with 8.8 g phosphorus pentasulfide, and heated under reflux for 5 hours. The pyridine is removed in vacuo and the residue is treated with water. The precipitate is filtered, washed with water, and recrystallized from ethanol to afford 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-1,5-dihydro-4H-imidazo-[4,5-cl]pyridine-4-thione.

Workup

  1. customevaporated in vacuo
  2. washThe ethyl acetate layer is washed with saturated NaHCO3
  3. dry with materialdried with MgSO4
  4. customRemoval of the ethyl acetate

Sources & evidence

ORD record
ord-eefe1e71aa4a440188145ee0d54f86cb
Source dataset
uspto-grants-1982_02
Patent number
US04315000

Reaction notes

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