Condensation of bifunctional 1-aminoisoindole with bis-electrophilic methyl 4-chloro-3-oxobutanoate undergoes regioselectively to afford 2-(chloromethyl)-2-hydroxy-2,6-dihydropyrimido[2,1-a]isoindol-4(3H)-one. The structure of the reaction product was unambiguously established by HMQC and HMBC heteronuclear correlations. The functionalization of the synthesized compound by reactions with a series of aliphatic amines was carried out.