Methyl iodide → 5-Thiazolecarboxylic acid, 2-[methyl(tetrahydro-2H-pyran-2-yl)amino]-, ethyl ester

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Reaction Steps

Ethyl 2-(tetrahydro-2H-pyran-2-ylamino)thiazole-5-carboxylate (4.73 g, 18.5 mmol) was added to a suspension of NaH (740 mg, 18.5 mmol) in THF (20 mL) at 0° C., followed by methyl iodide (1.15 mL, 18.5 mmol). The resulting mixture was heated at reflux during 3 hrs. After quenching with water and extracting with AcOEt, the crude product was purified by column chromatography (50% AcOEt/PE), yielding ethyl 2-(methyl(tetrahydro-2H-pyran-2-yl)amino)thiazole-5-carboxylate (2.02 g, 40%) as an oil.

Provenance & Evidence