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

HRID 398798

Reaction equation

HRID 398798 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) (20g, 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-aa3ab387bbd140b7b484e3b00f1c21fc
Source dataset
uspto-grants-1998_10
Patent number
US05817664

Linked notes

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