Water → (6-Chloro-5-nitro-pyrimidin-4-yloxy)-acetic acid methyl ester

HRID 1943724Notes

Reaction equation

HRID 1943724 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][OH:3].[H-].[Na+].[Cl:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14](Cl)[N:13]=[CH:12][N:11]=1.O>CN(C)C=O>[CH3:6][O:5][C:1](=[O:4])[CH2:2][O:3][C:14]1[C:15]([N+:16]([O-:18])=[O:17])=[C:10]([Cl:9])[N:11]=[CH:12][N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 203124,6-Dichloro-5-nitropyrimidineHCID 24758Sodium hydrideHCID 66774Methyl Glycolate

Product 1

HCID 86650561(6-Chloro-5-nitro-pyrimidin-4-yloxy)-acetic acid methyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a 50 ml flask at low temperature, methyl glycolate (0.22 ml, 2.8 mmol) and sodium hydride (114 mg, 2.8 mmol) were dissolved in N,N-dimethyl formamide (7 ml) and then stirred for 10 minutes. 4,6-dichloro-5-nitro-pyrimidine (500 mg, 2.6 mmol) dissolved in N,N-dimethyl formamide (6.5 ml) was added thereto dropwise and then stirred at the same temperature for additional 10 minutes, and then the temperature was raised to room temperature and stirred for additional 10 hours. After completion of the reaction by adding water, the mixture was extracted with dichloromethane, and the combined organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography eluting with a solvent of dichloromethane to obtain yellow liquid (280 mg, 44%).

Workup

  1. additionwas added
  2. stirringdropwise and then stirred at the same temperature for additional 10 minutes
  3. stirringstirred for additional 10 hours
  4. customAfter completion of the reaction
  5. extractionthe mixture was extracted with dichloromethane
  6. washthe combined organic layer was washed with saturated saline solution
  7. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography
  11. washeluting with a solvent of dichloromethane

Sources & evidence

ORD record
ord-a2eeefe68afa40be80af4826e12eba4f
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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