Synthesis of 4-substituted 2-(4-methylpiperazino)pyrimidines and quinazoline analogs as serotonin 5-HT2A receptor ligands

Jaroslaw Saczewski, Aldona Paluchowska, Jeffrey Klenc, Elizabeth Raux, Samuel Barnes, Shannon Sullivan, Beata Duszynska, Andrzej J. Bojarski, Lucjan Strekowskia

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68 Scopus citations

Abstract

(Chemical Equation Presented) The addition reaction of lithium reagents to the 4 position of 2-chloropyrimidine or 2-chloroquinazoline followed by oxidation of the resultant dihydro intermediate product is a powerful tool for the synthesis of 4-substituted 2-chloropyrimidines or 2-chloroquinazolines. 4-Vinyl derivatives undergo a conjugate nucleophilic addition across the vinyl group. A nucleophilic displacement of chloride in 4-substituted 2-chloropyrimidines or 2-chloroquinazolines by treatment with 4-methylpiperazine provides compounds that are antagonists of the serotonin 5-HT2A receptor.

Original languageEnglish (US)
Pages (from-to)1259-1265
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume46
Issue number6
DOIs
StatePublished - Nov 2009
Externally publishedYes

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