Bromine → HCID 5271380, compound

HRID 1981886Notes

Reaction equation

HRID 1981886 reaction equation
C([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11]C(=O)C2C=CC=CC=2)[O:8][C@@H:7]([N:20]2[CH:27]=[CH:26][C:24](=[O:25])[NH:23][C:21]2=[O:22])[C@H:6]1[F:28])(=O)C.C([O-])(=O)C.[Na+].[Br:34]Br>C(O)(=O)C>[F:28][C@H:6]1[C@H:5]([OH:4])[C@@H:9]([CH2:10][OH:11])[O:8][C@H:7]1[N:20]1[CH:27]=[C:26]([Br:34])[C:24](=[O:25])[NH:23][C:21]1=[O:22]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 70466634HCID 70466634, compound

Product 1

HCID 5271380HCID 5271380, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil (500 mg) and sodium acetate (100 mg) in 5 ml of glacial acetic acid is added a solution of bromine (240 mg) in 1 ml of glacial acetic acid. After 30 minutes at room temperature, the solvent is removed by evaporation in vacuo. Traces of acetic acid is removed by several co-evaporation with toluene. The residue is dissolved in saturated methanolic ammonia (50 ml) and the mixture is kept standing at room temperature for 2 days. The solvent is removed by evaporation in vacuo and the residue is crystallized from water to give 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-bromouracil (325 mg), m.p. 214°-216°.

Workup

  1. customthe solvent is removed by evaporation in vacuo
  2. customTraces of acetic acid is removed by several co-evaporation with toluene
  3. dissolutionThe residue is dissolved in saturated methanolic ammonia (50 ml)
  4. waitthe mixture is kept standing at room temperature for 2 days
  5. customThe solvent is removed by evaporation in vacuo
  6. customthe residue is crystallized from water

Sources & evidence

ORD record
ord-af540b036c894ed0914c833867d152ad
Source dataset
uspto-grants-1986_06
Patent number
US04594339

Reaction notes

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