5-Fluorouracil → HCID 15448748, compound

HRID 437036Notes

Reaction equation

HRID 437036 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[F:10]F.[F:12][C:13]([F:17])([F:16])[CH2:14][OH:15]>>[F:1][C:2]1([F:10])[CH:7]([O:15][CH2:14][C:13]([F:17])([F:16])[F:12])[NH:6][C:5](=[O:8])[NH:4][C:3]1=[O:9]

Participants

4

Reactant 3

HCID 33855-Fluorouracil2×HCID 64092,2,2-TrifluoroethanolHCID 24524Fluorine4×

Product 1

HCID 15448748HCID 15448748, compoundYield 79.5%

Procedure

5-fluorouracil (1.00 g, 0.0077 moles) was suspended in anhydrous 2,2,2-trifluoroethanol (20 ml) and treated with an equal volume mixture of gaseous fluorine and nitrogen at 68°-70° C. for 103 minutes at which time gaseous fluorine was detected leaving the reaction vessel, representing a consumption of 0.0182 moles of fluorine. The mole ratio of fluorine to 5-fluorouracil was 2.36. The solvent was removed under reduced pressure at room temperature (25° C.) to give a white solid which was dried at 50° C. at reduced pressure. The product was identified as 5,5-difluoro-5,6-dihydro-6-(2,2,2-trifluoroethoxy) uracil (1.67g) representing a yield of 79.5% with a melting point of 142°-146° C.; NMR confirmed the structure.

Workup

  1. customwas detected leaving the reaction vessel
  2. customThe solvent was removed under reduced pressure at room temperature (25° C.)
  3. customto give a white solid which
  4. customwas dried at 50° C. at reduced pressure

Sources & evidence

ORD record
ord-880c5dafd27d488c815fa9b21dacac86
Source dataset
uspto-grants-1977_06
Patent number
US04029661

Reaction notes

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