Synthesis of 4‐substituted 2‐(4‐methylpiperazino)pyrimidines and quinazoline analogs as serotonin 5‐HT_2A receptor ligands

Abstract

Abstract magnified image 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‐HT 2A receptor. J. Heterocyclic Chem., (2009).