5-(1-Propynyl)-2'-deoxyuridine → 5-Propynyluracil

HRID 1355551Notes

Reaction equation

HRID 1355551 reaction equation
[C:1]([C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H]1O[C@H](CO)[C@@H](O)C1)#[C:2][CH3:3]>P([O-])([O-])([O-])=O>[C:1]([C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[NH:8][CH:17]=1)#[C:2][CH3:3]

Participants

3

Reactant 1

HCID 4802655-(1-Propynyl)-2'-deoxyuridine

Product 1

HCID 1318135-Propynyluracil

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

To a stirred solution of 2′-deoxy-5-propynyluridine (European Patent Specification No. 272065) (20 g, 75 mmol) in aqueous phosphate buffer at pH 6.84 (1250 mL) was added purified E. coli thymidine phosphorylase (10,000 units) (T. A. Krenitsky et al, Biochemistry, 20, 3615, 1981; U.S. Pat. No. 4,381,344) and alkaline phosphatase (10,000 units) [Sigma type VII-S from bovine intestinal mucosa] and the whole mixture was incubated at 37° C. for 24 hours. The resulting white precipitate was filtered, washed with water (3×100 mL), ethanol (2×100 mL), ether (2×100 mL) and dried in vacuo over phosphorus pentoxide to give the title compound.

Workup

  1. custompurified E
  2. filtrationThe resulting white precipitate was filtered
  3. washwashed with water (3×100 mL), ethanol (2×100 mL), ether (2×100 mL)
  4. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-d1f4ecb07c8648e2b7ccac0486290fb4
Source dataset
uspto-grants-2003_07
Patent number
US06586440B2

Reaction notes

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