Potassium Hydroxide → {1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid

Participants

Reaction Steps

A white suspension of {1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid methyl ester (Intermediate B) (10 mg) in MeOH (300 μL) is treated with 5 M KOH (200 μL). The white suspension is left to stir at RT overnight. The reaction mixture is diluted with water to give a thick white precipitate which is filtered-off, washed with water and vacuum dried. The aqueous phase is acidified to pH 4 with dilute HCl followed by extraction with EtOAc (3×). The organic phase is dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as off-white solid. This is taken up in a minimal amount of DMF and purified further by reverse phase column chromatography (Isolute™ C18: 0-100% MeCN in water—0.1% TFA) to afford the title compound, [M+H]+ 448.

Provenance & Evidence