Potassium Hydroxide → {5-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

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Reaction Steps

To 5H-Pyrrolo[2,3-b]pyrazine (3, 0.150 g, 1.26 mmol) in 2.2 mL of methanol, (5-formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (6, 0.52 g, 1.5 mmol) and potassium hydroxide (0.230 g, 4.10 mmol) were added. The reaction was allowed to stir at room temperature overnight, then concentrated and poured into saturated sodium bicarbonate, and extracted with ethyl acetate. The organic portion was washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum and purified by silica gel chromatography to provide the desired compound (7, 0.22 g, 38%).

Provenance & Evidence