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Paper | Regular issue | Vol 81, No. 3, 2010, pp.611-623
Published online, 1st February, 2010
DOI: 10.3987/COM-09-11881
Synthesis of 3-(Pyrimidinyl)pyrrole Derivatives

Igor Yu. Nestorak, Anton V. Tverdokhlebov,* Andrey A. Tolmachev, and Yulian M. Volovenko

*Enamine Ltd. Co., Alexandra Matrosova Str. 23, 01103 Kiev, Ukraine


Alkylation of 4,6-dimethyl-2-pyrimidineacetonitrile and 2,6-dimethyl-4-pyrimidineacetonitrile with chloroacetic acid anilides was shown to give 5-amino-4-(4,6-dimethyl-2-pyrimidinyl)-2,3-dihydro-1-arylpyrrol-2-ones and 5-amino-4-(2,6-dimethyl-4-pyrimidinyl)-2,3-dihydro-1-arylpyrrol-2-ones, respectively. Corresponding isomeric compounds, 5-amino-4-pyrimidinyl-2,3-dihydropyrrol-3-ones were obtained by Claisen condensation of the mentioned pyrimidineacetonitriles with N-Boc α-aminoacids imidazolides followed by removal of the protecting group accompanied with simultaneous ring closure.