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

Participants

Reaction Steps

To a stirred suspension of 1.7 g (4.2 mmol) 1-benzoyl-3-{2-methoxy-5-[methyl-(tetrahydro-pyran-4-yl)-amino]-phenyl}-thiourea in 13 ml methanol was added dropwise 0.78 ml (6.35 mmol) 5.4 M sodium methylate solution and stirring continued for 18 hrs at room temperature. The mixture was then concentrated in vacuo and the residue subjected to column chromatography (1/1 hexane/ethyl acetate) to afford 0.6 g (51%) {2-methoxy-5-[methyl-(tetrahydro-pyran-4-yl)-amino]-phenyl}-thiourea as a yellow solid. ES-MS m/e (%): 296 (M+H+, 100).

Provenance & Evidence