2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(3,4-Methylenedioxy-phenyl)-2-[5-(4-methoxyphenyl)-pyrimidin-2-yl-]-4-hydoxy-2,3,4,9-tetrahydro-1H-beta-carboline

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To a mixture of DDQ (113.5 mg, 0.5 mmol) and 1-(3,4-methylenedioxyphenyl)-2-[5-(3,4-dimethoxyphenyl)pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-β-carboline (prepared as in Example 3) (51 mg, 0.1 mmol) was added a mixed solvent of THF:water (9:1) at −78° C. The mixture was stirred at 0° C. and allowed to warm to room temperature over a period of 15 h. Column chromatography (silica gel, hexanes:ethyl acetate=1:1) yielded the-oxo- and -hydroxy derivatives respectively, as white solids.

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