2-Amino-6-chloro-4-(N-methylpiperazino)pyrimidines, inhibitors of spiroperidol binding

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Abstract
A series of thirty 6-chloro-2,4-diaminopyrimidines was synthesized and tested in rat striatal membranes as inhibitors of [3H]spiroperidol binding. The affinity for the dopamine receptor was related to the 6-chloro-4-(N-methylpiperazine)pyrimidine structure bearing an NH2 or NHR1 group as a substituent in position 2, provided that R1 was not an .alpha. branched alkyl group. The nature of the substituent in position 5 is also of importance for the affinity; 2-(benzylamino)-6-chloro-4-(N-methylpiperazino)-5-(methylthio)pyrimidine is the most active member of the series. Molecular structures of 3 compounds were analyzed by X-ray diffraction and PCILO [perturbative configuration using localized orbitals] computation.