HCID 89545449, compound → HCID 136508799, compound

Participants

Reaction Steps

A suspension of 5-chloro-2-hydroxy-N-(pyrazin-2-ylmethyl)benzamide (0.38 g, 1.4 mmol) in a mixture of 1,2-dichloroethane (6 mL) and phosphoryl chloride (6 mL) was heated at reflux for 2 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was suspended in water (10 mL), and the pH was adjusted to 6-7 with 1 N aqueous sodium hydroxide. The aqueous phase was extracted with ethyl acetate (3×30 mL) followed by dichloromethane (3×40 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 0-10% gradient of methanol in dichloromethane to afford 4-chloro-2-(imidazo[1,5-a]pyrazin-3-yl)phenol as a pale yellow solid in 18% yield (0.064 g): MS (ES+) m/z 245.9 (M+1), 247.9 (M+1).

Provenance & Evidence