Sodium Hydroxide → HCID 57654610, compound

Participants

Reaction Steps

Sodium hydroxide [2N] (0.59 mL) was added to a solution of 2-[3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-malonic acid diethyl ester (0.250 g, 0.590 mmol) in methanol (5 mL) and stirred at room temperature for several hours. The crude reaction was then evaporated in vacuo, 1N HCl was added and the product was extracted with ethyl acetate to give 0.141 g of [3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-acetic acid methyl ester. This was dissolved in a mixture of toluene/methanol [8/1] (3 mL) and trimethylsilyldiazomethane [2.0M] (0.22 mL) was added at room temperature and stirred until bubbling has stopped. The reaction was then evaporated in vacuo and purified via silica gel column chromatography in hexane:ethyl acetate (1:1) to give 0.119 g (60%) of [3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-acetic acid methyl ester. Mass spectrum (LCMS, ESI pos.): Calcd for C19H18N2O4; found: 339.1, 340.1 (M+H).

Provenance & Evidence