Using 5-chloro-2,4,6-trifluoropyrimidine for Pyrimidine Synthesis
Author Information
Author(s): Emma L Parks, Graham Sandford, Christopher John A, David D Miller
Primary Institution: Department of Chemistry, University of Durham
Hypothesis
Can 5-chloro-2,4,6-trifluoropyrimidine serve as an effective scaffold for synthesizing functionalized pyrimidine derivatives?
Conclusion
5-Chloro-2,4,6-trifluoropyrimidine is not ideal for multiple substitution processes due to the need for purification to remove unwanted isomers, but it can yield 4-amino derivatives in acceptable yields.
Supporting Evidence
- 5-Chloro-2,4,6-trifluoropyrimidine can react with nitrogen nucleophiles to form various products.
- Purification is necessary to isolate the desired 4-amino derivatives from the reaction mixture.
- Reactions were monitored using 19F NMR to determine product ratios.
Takeaway
The study looks at how a specific chemical can be used to make new medicines, but it turns out that it's not the best choice because it creates some unwanted products that need to be cleaned up.
Methodology
Reactions were conducted with various nitrogen nucleophiles in acetonitrile at 0 °C, monitored by 19F NMR.
Limitations
Purification is required to remove the 2-substituted regioisomer before further reactions.
Digital Object Identifier (DOI)
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