Sodium ethoxide → HCID 66933435, compound

HRID 2069394Notes

Reaction equation

HRID 2069394 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH2:12][CH3:13])[N:9]=[C:8](S(C)(=O)=O)[N:7]=1)=[O:5])C.[CH3:18][CH2:19][O-:20].[Na+]>C(O)C>[CH2:19]([O:20][C:8]1[N:7]=[C:6]([C:4]([OH:3])=[O:5])[CH:11]=[C:10]([CH2:12][CH3:13])[N:9]=1)[CH3:18]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 66933549HCID 66933549, compound

Product 1

HCID 66933435HCID 66933435, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-ethyl-2-methanesulfonyl-pyrimidine-4-carboxylic acid ethyl ester (100 mg, 0.39 mmol) in ethanol (4 mL), sodium ethylate (134 mg, 1.94 mmol) is added. The reaction mixture is stirred for 2 h, ethanol is evaporated and the residue is dissolved in EtOAc (25 mL). The org. solution is washed with 1M aq. KHSO4, followed by brine, dried over MgSO4, filtered and evaporated give 2-ethoxy-6-ethyl-pyrimidine-4-carboxylic acid as a yellow oil (35 mg); LC-MS: tR=0.72 min, [M+H]+=197.07.

Workup

  1. customethanol is evaporated
  2. dissolutionthe residue is dissolved in EtOAc (25 mL)
  3. washsolution is washed with 1M aq. KHSO4
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-02de8fccdf3a49e6850b323b913695a6
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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