Sodium hydride → (5-(2-Chloropyridin-4-yloxy)-4,6-dimethylpyridin-3-yl)methanol

Participants

Reaction Steps

A suspension of sodium hydride (5.27 g, 209 mmol) in DMF (100 mL) was carefully charged with 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride (18 g, 95 mmol). The mixture stirred at ambient temperature for 2 hours. 2-chloro-4-nitropyridine (15 g, 95 mmol) was then added and the reaction stirred overnight at ambient temperature. The material was diluted with water and extracted with ethyl acetate. The organic layer was dried, and concentrated. Flash chromatography (dichloromethane/methanol 20:1) gave the title compound (19.8 g, 79%) as colorless oil.

Provenance & Evidence