Water → 6-(2-Bromobenzyl)-1-(2-methylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

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Reaction Steps

2.0 g (9.25 mmol) of 5-amino-1-(2-methylphenyl)-1H-pyrazole-4-carboxamide (Example 25A) and 9.5 g (41.62 mmol) of methyl (2-bromophenyl)acetate are dissolved in 30 ml of absolute ethanol under argon, and 3.15 g (46.6 mmol) of sodium ethoxide are added. The reaction mixture is heated to a reflux overnight. Cooling to room temperature is followed by hydrolysis with 50 ml of water and subsequent extraction with ethyl acetate (2×50 ml). The combined organic phases are dried over sodium sulphate, and the solvent is distilled off under reduced pressure. The crude product is then purified by column chromatography (silica gel; mobile phase cyclohexane/ethyl acetate, gradient 10:1→1:1). 3.01 g (82% of theory) of the product are obtained.

Provenance & Evidence