Thymine → 5-Fluoro-5-methyluracil
Reaction equation
[CH3:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[F:10]F.N#N.FF>FC(F)(F)C(O)=O>[F:10][C:2]1([CH3:1])[CH:7]=[N:6][C:5](=[O:8])[NH:4][C:3]1=[O:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 14 °C
Procedure
5-methyluracil (1.00 g) in trifluoroacetic acid (10 ml) was treated with gaseous fluorine-nitrogen mixture. The reaction began at an initial temperature of 0° C. and during the fluorination the reaction temperature was raised to 14° C. and the reaction continued until completion for 120 minutes. The mole ratio of fluorine to 5-methyl-uracil was 2.56. The solvent was evaporated at about 50° C. under reduced pressure leaving a brown solid, which upon extracting with acetone gave 5-fluoro-5-methyluracil (0.21g) whose structure was confirmed by NMR analysis.
Workup
- customtemperature of 0° C.
- customThe solvent was evaporated at about 50° C. under reduced pressure
- customleaving a brown solid, which
- extractionupon extracting with acetone
Sources & evidence
- ORD record
- ord-1a32157493194d0c9c1e81806ed73d41
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04029661
Reaction notes
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