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Start Over Author "Bart Geurtsen" Journal journal of the chemical society, perkin transactions 1
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1. Photoreactivity of diazines. Part III. Pyrimidines. Part XXXVIII. Photoamination of halogenopyrimidines

Author

Dick A. de Bie, Bart Geurtsen, and Henk C. van der Plas

Subjects
Solvent, Part iii, Nitroxide mediated radical polymerization, Chemistry, Liquid ammonia, Reactivity (chemistry), Photochemistry, Inhibitory effect, Medicinal chemistry, Amination, Scavenger (chemistry)
Abstract

The hitherto unknown u.v. induced amination of 4-X-6-phenylpyrimidines (V; X = Cl, Br, or I) to give 4-amino-6-phenylpyrimidine (VI), using liquid ammonia as solvent and reactant, is described. The reactivity order is found to be I > Br > Cl. Evidence is presented that the photoamination does not occur according to an SN(ANRORC) or an SN(AE) mechanism. Since an inhibitory effect of the radical scavenger di-t-butyl nitroxide is observed in the photoamination, a reaction pathway involving a radical as intermediate is postulated.

Published
1974
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