Abstract
A series of new fluorine containing 4-amino-pyrimidine-5-carbonitrile derivatives has been synthesised from the three-component reaction of malononitrile, fluorinated aldehydes or ketone and N-unsubstituted amidines. The reaction occurs in water at reflux and is microwave assisted. This method provides a new route to produce fluorinated pyrimidine derivatives in good to excellent yields.
Keywords
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