Potassium Hydroxide → 1-(6-benzoylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid

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Reaction Steps

Aqueous 1M KOH (1.06 mL, 1.06 mmol) was added to 1-(6-benzoylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.142 g, 0.343 mmol) in THF (1.0 mL). The reaction mixture was allowed to stir at room temperature for 18 h and was then concentrated. The residue was redissolved in water (5 mL) and brought to pH 1 with aqueous 1M HCl (3 mL). The resulting precipitate was collected by filtration to yield the titled compound (0.110 g, 82% yield). MS (ESI/Cl): mass calcd. for C19H13N5O4, 375.1; m/z found, 376.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 12.99 (s, 1H), 12.79 (s, 1H), 10.60 (s, 1H), 8.95 (s, 1H), 8.68 (s, 1H), 8.26 (s, 1H), 8.23 (dd, J=8.8, 2.4 Hz, 1H), 8.04-7.99 (m, 2H), 7.71 (d, J=7.8 Hz, 1H), 7.65-7.60 (m, 1H), 7.59-7.54 (m, 2H).

Provenance & Evidence