Photolysis of 5-iodopyrimidines in benzene or heteroarenes; a convenient route to 5-phenyl- and 5-heteroaryl-pyrimidines
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 621-624
- https://doi.org/10.1039/p19770000621
Abstract
Photolysis of 5-iodo-, 2-chloro-5-iodo-, and 2,4-dichloro-5-iodo-pyrimidine in solutions of heteroarenes (furan, thiophen, pyrrole, and 1-methylpyrrole) or benzene in acetonitrile affords conveniently and in high yield the corresponding 5-(2-heteroaryl)- and 5-(phenyl)-pyrimidines (1)–(3)(X = O, S, NH, NMe, or CHCH). Only for those photolyses carried out in thiophen are small amounts of the 3-heteroaryl isomers formed. In contrast, photolysis of the relatively unstable 4-chloro-5-iodopyrimidine in solutions of the above heteroarenes or benzene in acetonitrile gives only low yields of the 4-chloro-5-substituted pyrimidines.Keywords
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