Acetic Anhydride → 5-Ethynyluridine

HRID 645344Notes

Reaction equation

HRID 645344 reaction equation
I[C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9].[C:19](OC(=O)C)(=O)[CH3:20]>N1C=CC=CC=1>[C:19]([C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9])#[CH:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12681085-Iodouridine

Product 1

HCID 148859605-Ethynyluridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A dry 250 mL round-bottomed flask was charged with 5-iodouridine (10 g, 27 mmol Aldrich), anhydrous pyridine (30 mL) and acetic anhydride (30 mL). The reaction was stirred at room temperature for 30 minutes under a nitrogen atmosphere and the solvent removed in vacuo. The compound was diluted with toluene (2×50 mL) and the toluene removed in vacuo. The product was purified on a 75 g flash chromatography column which was eluted with 90:10 (v:v) CHCl3:MeOH. The appropriate fractions were combined and concentrated to give the title compound as a white foam. This was used directly in the next stage.

Workup

  1. customthe solvent removed in vacuo
  2. additionThe compound was diluted with toluene (2×50 mL)
  3. customthe toluene removed in vacuo
  4. customThe product was purified on a 75 g flash chromatography column which
  5. washwas eluted with 90:10 (v:v) CHCl3
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55237e1acd754768ba18d67c0191e07a
Source dataset
uspto-grants-2010_04
Patent number
US07704971B2

Reaction notes

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