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

HRID 378818

Reaction equation

HRID 378818 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.coli thymidine phosphorylase (10,000 units) (T
  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-823f2974547e42e2b5acf7bb71c16bc3
Source dataset
uspto-grants-2001_10
Patent number
US06297223B1

Linked notes

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