Dimethyl Sulfoxide → HCID 21217687, compound

Participants

Reaction Steps

A mixture of 1-ethyl-6-hydroxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (0.5 g, 1.5 mmol), DMSO (5 ml) and KOH (0.5 g) is stirred at room temperature for 20 minutes, then ethyl 2-bromopropionate (0.2 ml) is added, and the mixture is stirred overnight. The reaction mixture is poured into 10 volumes of water, extracted with CH2Cl2 (2×10 ml), and the aqueous layer is acidified with acetic acid. A precipitate forms which is collected by filtration, dissolved in methanol and filtered. The filtrate is allowed to stand, and the product that precipitates is collected by filtration and dried to afford 180 mg of 1-ethyl-6-(1-carboxyethoxy)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine. 1/4 Hydrate, m.p. 280° C. (dec.).

Provenance & Evidence