Pyridine → 5-Propynyluracil

HRID 398801Notes

Reaction equation

HRID 398801 reaction equation
I[C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O.C(OC(=O)C)(=O)C.N1C=C[CH:29]=[CH:28][CH:27]=1>>[C:27]([C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[NH:6][CH:16]=1)#[C:28][CH3:29]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 12681085-Iodouridine

Product 1

HCID 1318135-Propynyluracil

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 (30mL). 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) CHC13 :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)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-41a47d6b1e074f9e8493d6a6e5e5a587
Source dataset
uspto-grants-1998_10
Patent number
US05817664

Reaction notes

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