Trifluoroacetic acid → 5-Fluorouracil

HRID 1112489Notes

Reaction equation

HRID 1112489 reaction equation
[NH:1]1[CH:8]=CC(N)=[N:4][C:2]1=[O:3].FS(O)(=O)=O.[F].[F:15][C:16](F)(F)[C:17]([OH:19])=O>O>[F:15][C:16]1[C:17](=[O:19])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 178418229CytosineHCID 178527664HCID 178527664, compound

Product 1

HCID 33855-Fluorouracil

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a solution of cytosine (11.1 g) in a mixture of trifluoracetic acid (80 ml) and water (10 ml) kept at 10° C., fluorine fluorosulfonate was blown while stirring. The cytosine was completely consumed in 90 minutes, and the total amount of fluorine fluorosulfonate used was 18 mmol. The reaction mixture was heated under reflux for 4 hours and then treated as in Example 11 to give 5-fluorouracil (10.4 g). Yield, 80%.

Workup

  1. customkept at 10° C.
  2. customThe cytosine was completely consumed in 90 minutes
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 4 hours
  5. additiontreated as in Example 11

Sources & evidence

ORD record
ord-d85e41cb4be144a1a9ba0b8269516299
Source dataset
uspto-grants-1978_10
Patent number
US04122251

Reaction notes

Loading…