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

HRID 1447002
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1447002
[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]
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Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049
Pyridine
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-eefe1e71aa4a440188145ee0d54f86cb
Quelldatensatz
uspto-grants-1982_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04315000

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