Riboflavin → 4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline

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A solution of 4-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline (1.09 g, 4.0 mmol) in ethanol (40 mL) was added palladium hydroxide, 20 wt. % Pd (dry basis) on carbon, wet, Degussa type E101 NEW (0.284 g, 0.405 mmol) and hydrogenated (double-walled balloon pressure) at room temperature for 4 h. The reaction mixture was filtered via a pad of Celite, and the filtrate was concentrated in vacuo and chromatographed via flash column chromatography (20% to 80% EtOAc/Hexanes) to give 4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline (0.648 g, 59% yield) as a white solid. [M+1]=272.0.

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