Coupling of chloroquinazoline (I) with 3-bromoaniline (II) in refluxing isopropanol yielded anilinoquinazoline (III). The nitro group was then reduced with Fe dust and AcOH in aqueous ethanol to give amine (IV). Finally, condensation with acrylic acid (V) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (EDC) in DMF provided the target acrylamide.
Arylamine (I) is converted into the corresponding methyltriazene (II) by formation of the corresponding diazonium salt with NaNO2 in HCl/H2O, followed by reaction with methylamine. Finally, the target compound is obtained by coupling of (II) with the corresponding amine in refluxing isopropanol.