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

HRID 566942

Reaction equation

HRID 566942 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. Patent Specification 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.A. Krenitsky et al, Biochemistry, 20, 3615, 1981; U.S. Patent Specification No. 4,381,344) and alkaline phosphatase (10,000 units) [Sigma type VII-S from bovine intestinal mucosa]
  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-802da74093fe40879c826ce9c075a370
Source dataset
uspto-grants-2001_01
Patent number
US06177436B1

Linked notes

Loading…