Pyridine → Methyl 5-chloropyrazine-2-carboxylate

Participants

Reaction Steps

Reflux a mixture of 5-Hydroxy-pyrazine-2-carboxylic acid (6.568 g, 46.88 mmol), thionyl chloride (51 mL, 703.2 mmol), and DMF (0.50 mL) for 4 h. Cool the mixture to room temperature, concentrate in vacuo, and pump on high vacuum for 3 h. Dilute the mixture with MeOH (25 mL) and add pyridine (4.5 mL, 55.7 mmol). Stir the mixture overnight at room temperature. Adsorb the reaction mixture onto silica gel and subject the mixture to flash column chromatography (330 g column, 25%-60% ethyl acetate/n-hexane) to yield the desired product (7.380 g, 91%). mass spectrum (m/e): 173.0 (M+1).

Provenance & Evidence