Tegafur → HCID 22150346, compound

HRID 703561Notes

Reaction equation

HRID 703561 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5](Cl)=[O:6])[CH:3]=1.C(N(CC)CC)C.[F:20][C:21]1[C:22](=[O:33])[NH:23][C:24](=[O:32])[N:25]([CH:27]2[CH2:31][CH2:30][CH2:29][O:28]2)[CH:26]=1.[OH:34][C:35]1[CH:40]=[CH:39][NH:38][C:37](=[O:41])[CH:36]=1>O1CCOCC1>[O:41]=[C:37]1[CH:36]=[C:35]([O:34][C:1]([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([N:23]2[C:22](=[O:33])[C:21]([F:20])=[CH:26][N:25]([CH:27]3[CH2:31][CH2:30][CH2:29][O:28]3)[C:24]2=[O:32])=[O:6])=[O:11])[CH:40]=[CH:39][NH:38]1

Participants

6

Reactant 4

HCID 5386TegafurHCID 7451Isophthaloyl chlorideHCID 8471Triethylamine2×HCID 546960044-Hydroxy-2(1H)-pyridinone

Product 1

HCID 22150346HCID 22150346, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1.00 g quantity of isophthaloyl chloride and 0.70 ml of triethylamine were added to a solution of 1.00 g of 5-fluoro-1-(2-tetrahydrofuranyl)uracil in 30 ml of dried dioxane. The mixture was refluxed for 2 hours. Thereto added was 1.00 ml of triethylamine and the mixture was refluxed for 2 hours. Thereto further added was 0.60 g of 4-hydroxy-2(1H)-pyridone and the mixture was refluxed for 3 hours. The solvent was distilled off and 30 ml of ethyl acetate and 30 ml of water were added to the residue. The insolubles were removed by filtration. The ethyl acetate layer was separated, dried over anhydrous sodium sulfate and concentrated. The concentrate was subjected to silica gel column chromatography to conduct gradient elution using chloroform and mixtures of methanol (up to 2%) and chloroform. The fractions corresponding to the title compound were collected and concentrated, giving 0.40 g of a powder in a yield of 18%.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. additionThereto added
  3. temperaturethe mixture was refluxed for 2 hours
  4. additionThereto further added
  5. temperaturethe mixture was refluxed for 3 hours
  6. distillationThe solvent was distilled off
  7. addition30 ml of ethyl acetate and 30 ml of water were added to the residue
  8. customThe insolubles were removed by filtration
  9. customThe ethyl acetate layer was separated
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. washelution
  13. customThe fractions corresponding to the title compound were collected
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-b951b3381c0347d18485fea1b9544ca5
Source dataset
uspto-grants-1991_01
Patent number
US04983609

Reaction notes

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