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Über N1- und N2-substituierte 2-Amino-5,6-dihydro-4(1H)-pyrimidinone

N1- and N2-substituted 2-amino-5,6-dihydro-4(1H)-pyrimidinones (heterocyclic compounds, 79)

Über Heterocyclen, 79. Mitteilung

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

The reactions of the monosubstituted guanidines2 b-h with methyl acrylate in dimethylformamide or ethanol as solvent preferentially afford 1-substituted 2-amino-5,6-dihydro-4(1H)-pyrimidinones6 b-h. The structures of 1-hexyl- and 1-benzyl-4-pyrimidinones6 c, e and of the picrate of 1-phenylpyrimidinone6 g were proved by comparison with authentic samples, which were prepared from N-substituted ethyl 3-amino-propionates14 c, e andg and cyanamide. Accordingly,6 g is not identical with authentic 2-phenylaminopyrimidinone7 g (prepared from 2-methylthio-4-pyrimidinone10 and 2-thioxo-4-pyrimidinone12 respectively, compare10).

N,N-Disubstituted guanidines2 i-m react with methyl acrylate in dimethylformamide as solvent to afford N2,N2-disubstituted 2-amino-5,6-dihydro-4-(1H)-pyrimidinones7 i-m. Action of morpholine-4-carboxamidine (21) on methyl acrylate in ethanol yields 2-morpholinopyrimidinone71 as byproduct and 3-ethoxy-N-[morpholino(amino)methylene]propionamide (91) as mainproduct.

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  1. Institut für Pharmazeutische Chemie, Universität Graz, A-8010, Graz, Österreich

    Winfried Wendelin & Renate Riedl

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  1. Winfried Wendelin
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  2. Renate Riedl
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Herrn Prof. Dr.Robert Ott mit den besten Wünschen zum 60. Geburtstag gewidmet.

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Wendelin, W., Riedl, R. Über N1- und N2-substituierte 2-Amino-5,6-dihydro-4(1H)-pyrimidinone. Monatsh Chem 116, 237–251 (1985). https://doi.org/10.1007/BF00798460

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  • DOI: https://doi.org/10.1007/BF00798460

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