Sodium Methoxide → HCID 11406981, compound

HRID 1951233Notes

Reaction equation

HRID 1951233 reaction equation
[CH3:1][O-:2].[Na+].[CH2:4]([C:6]1[O:10][C:9]([CH2:11][CH2:12][NH:13][C:14]([NH:16][C:17]2[S:18][C:19]([C:23]3[CH:28]=[C:27]([CH3:29])[N:26]=[C:25](S(C)=O)[N:24]=3)=[C:20]([CH3:22])[N:21]=2)=[O:15])=[N:8][CH:7]=1)[CH3:5]>CO>[CH2:4]([C:6]1[O:10][C:9]([CH2:11][CH2:12][NH:13][C:14]([NH:16][C:17]2[S:18][C:19]([C:23]3[CH:28]=[C:27]([CH3:29])[N:26]=[C:25]([O:2][CH3:1])[N:24]=3)=[C:20]([CH3:22])[N:21]=2)=[O:15])=[N:8][CH:7]=1)[CH3:5]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 11281950HCID 11281950, compound

Product 1

HCID 11406981HCID 11406981, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (2M in MeOH, 0.115 ml, 0.23 mmol) is added to a stirred solution of 1-[2-(5-ethyl-oxazol-2-yl)-ethyl]-3-[5-(2-methanesulfinyl-6-methyl-pyrimidin-4-yl)-4-methyl-thiazol-2-yl]-urea (Example 40) (0.050 g, 0.115 mmol) in methanol (3 ml) at room temperature. After 18 hours, the solvent is removed and the residue is dissolved in DCM and washed with water. The product is extracted into 1M HCl and the aqueous extract is washed with DCM. The aqueous phase is then basified with aq. NaOH and the product is extracted into DCM. After drying MgSO4) the solvent is removed to give the titled compound.

Workup

  1. customthe solvent is removed
  2. dissolutionthe residue is dissolved in DCM
  3. washwashed with water
  4. extractionThe product is extracted into 1M HCl
  5. extractionthe aqueous extract
  6. washis washed with DCM
  7. extractionthe product is extracted into DCM
  8. dry with materialAfter drying MgSO4) the solvent
  9. customis removed

Sources & evidence

ORD record
ord-454c2591a4c241d0853aafdb0c4f7996
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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