Heterocyclic studies. Part XII. Trichloro-6-cyanopyrimidine
Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39690002780
Abstract
Treatment of 4-carbamoyl-2,6-dihydroxy-5-nitropyrimidine (I; X = CONH2) with phosphoryl chloride and diethylaniline unexpectedly yielded 2,4,5-trichloro-6-cyanopyrimidine (III; X = CN) together with 4-carbamoyl-2,6-dichloro-5-nitropyrimidine (II; X = Cl, Y = CONH2) and a little 2-chloro-4-cyano-6-N-ethylanilino-5-nitropyrimidine (II; X = NEtPh, Y = CN). Some of the trichloro-cyano-pyrimidine was also obtained by treatment of the pyrimidine (I; X = CONH2) with phosphoryl chloride in the presence of dimethylaniline, pyridine, triethylamine, or phosphorus pentachloride.
Nucleophilic substitution reaction of trichloro-6-cyanopyrimidine, in which the cyano-group was often displaced first, or modified, are described.
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Journal Name：Journal of the Chemical Society C: Organic
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CAS no.: 89640-58-4
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