86604-75-3

White Solid

Intermediate in the production of the antiulcer agent Omeprazole

The general procedure for the synthesis of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride from 4-methoxy-3,5-dimethyl-2-hydroxymethylpyridine was as follows: to a solution of 4-methoxy-3,5-dimethyl-2-hydroxymethylpyridine (25.1 g, 0.15 mol) in dichloromethane (400 mL) was added slowly and dropwise thionyl chloride (18.8 g, 0.158 mol) in dichloromethane (100 mL). 0.158 mol) to a solution of thionyl chloride (18.8 g, 0.158 mol) in dichloromethane (100 mL). The reaction was carried out at room temperature and under argon protection, and the titration process lasted for 30 minutes. After the dropwise addition, the reaction was continued with stirring at room temperature for 30 minutes. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The solid residue obtained was suspended in hexane (200 mL) and the solid was collected by filtration. The solid was washed with hexane (50 mL) and subsequently dried in air to afford 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride 33.3 g (100% yield) as a white solid.

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[4] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1777 - 1788
[5] Patent: US5292886, 1994, A