4-[(1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethyl]-6-(methyloxy)-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one → 4-[(1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethyl]-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one

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Reaction Steps

A solution of 4-[(1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethyl]-6-(methyloxy)-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one (494.1 g, 1.34 mol) and MnO2 (584.4 g, 6.72 mol) in DCM (18 L) was stirred at room temperature for 1 h. The mixture was filtered through celite and the filtrate was evaporated to give a purple/white solid. The crude was purified by column chromatography and mixtures of heptane and EtOAc as eluent to give of 451.6 g (66%) of 4-[(1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethyl]-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one.

Provenance & Evidence