Sodium Methoxide → {2-Methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea

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Reaction Steps

To a stirred suspension of 2.0 g (4.8 mmol) 1-benzoyl-3-{2-methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea in 15 ml methanol was added dropwise 0.4 ml (7.25 mmol) 5.4 M sodium methylate solution and stirring continued for 18 hrs at room temperature. The mixture was then concentrated in vactio and the residue subjected to column chromatography (1/1 hexane/ethyl acetate) to afford 1.5 g (100%) {2-methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea as a beige oil. ES-MS m/e (%): 310 (M+H+, 100).

Provenance & Evidence