Carbon Dioxide → 5-Fluorouracil

HRID 2052723Notes

Reaction equation

HRID 2052723 reaction equation
O.[F:2][C:3]1[C:11](=[O:12])[NH:10][C:9](=[O:13])[NH:8][C:4]=1C(O)=O.O.C(=O)=O>COCCOCCOCCOC>[F:2][C:3]1[C:11](=[O:12])[NH:10][C:9](=[O:13])[NH:8][CH:4]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 962WaterHCID 162127495-Fluoroorotic acid hydrate 98

Product 1

HCID 33855-FluorouracilYield 90%

Reagents, catalysts & solvents 1

HCID 8189TriglymeSolvent

Conditions

Temperature
200 °C

Procedure

In the example, 20 g of crystals of 5-fluoro-orotic acid monohydrate obtained by the fluorination and the post-treatment of Example 1 was suspended in 80 ml of triethyleneglycol dimethyl ether and the mixture was heated under stirring whereby water was generated at higher than 130° C. and carbon dioxide was generated at higher than 190° C. The decarboxylation was completed by heating at 200° C. for about 20 minutes. After cooling the reaction mixture, the reaction product was separated by a filtration and recrystallized from water to obtain 12.2 g of 5-fluorouracil. The yield was 90% based on 5-fluoro-orotic acid monohydrate.

Workup

  1. temperaturethe mixture was heated
  2. customhigher than 130° C.
  3. customhigher than 190° C
  4. temperatureAfter cooling the reaction mixture
  5. customthe reaction product was separated by a filtration
  6. customrecrystallized from water

Sources & evidence

ORD record
ord-4ab561071aba4f28adc0a3e58e9f57ef
Source dataset
uspto-grants-1980_01
Patent number
US04186266

Reaction notes

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