Monatshefte für Chemie / Chemical Monthly

, Volume 116, Issue 2, pp 237–251 | Cite as

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

Über Heterocyclen, 79. Mitteilung
  • Winfried Wendelin
  • Renate Riedl
Organische Chemie Und Biochemie

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

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.

Keywords

Acrylic acid methylester, reactions Guanidines, mono- and N,N-disubstituted Propionamide, 3-ethoxy-N-[morpholino(amino)methylene] 4 (1H)-Pyrimidinones, 2-amino Pyrimidine-1-propionic acid ethylester, hexahydro-4-oxo-2-thioxo 

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Copyright information

© Springer-Verlag 1985

Authors and Affiliations

  • Winfried Wendelin
    • 1
  • Renate Riedl
    • 1
  1. 1.Institut für Pharmazeutische ChemieUniversität GrazGrazÖsterreich

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