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

HRID 51899Notes

Reaction equation

HRID 51899 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([N:19]([CH3:26])[CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:16]=[CH:15][C:14]=1[O:27][CH3:28])=[S:11])(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[CH3:28][O:27][C:14]1[CH:15]=[CH:16][C:17]([N:19]([CH3:26])[CH:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)=[CH:18][C:13]=1[NH:12][C:10]([NH2:9])=[S:11]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22736981HCID 22736981, compound

Product 1

HCID 22736964{2-Methoxy-5-[methyl-(tetrahydro-pyran-4-yl)-amino]-phenyl}-thioureaYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-592077d2cbdb44d2a610fccf5bea13b1
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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