Ethyl Propionate → HCID 21329206, compound

HRID 614377Notes

Reaction equation

HRID 614377 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[N:8]=[CH:7][N:6]=[C:5]([C:9]([O:11]CC)=O)[CH:4]=1.[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:16][CH3:17].[H-].[Na+]>COCCOC>[CH3:14][N:2]([CH3:1])[C:3]1[N:8]=[CH:7][N:6]=[C:5]([C:9](=[O:11])[CH:16]([CH3:17])[C:15]([O:19][CH2:20][CH3:21])=[O:18])[CH:4]=1

Participants

5

Reactant 3

HCID 7749Ethyl PropionateHCID 24758Sodium hydrideHCID 21329164HCID 21329164, compound

Product 1

HCID 21329206HCID 21329206, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 6-dimethylamino-4-ethoxycarbonylpyrimidine (19.5 g) and ethyl propionate (11.2 g) in 1,2-dimethoxyethane (75 cc) is added to a suspension of sodium hydride (9.6 g) (50% in mineral oil) in 1,2-dimethoxyethane (25 cc), and the reaction mixture is refluxed. Refluxing is maintained for a further 30 minutes. The solvent is evaporated, and then the residue is taken up in diethyl ether (350 cc) and 4N hydrochloric acid (70 cc). After decanting, the aqueous phase is again extracted with diethyl ether (450 cc). The combined organic phases are washed with an 8% (w/v) sodium bicarbonate solution (120 cc). They are dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure to give ethyl 3-(6-dimethylaminopyrimidin-4-yl)-2-methyl-3-oxopropionate (15.2 g).

Workup

  1. temperaturethe reaction mixture is refluxed
  2. temperatureRefluxing
  3. temperatureis maintained for a further 30 minutes
  4. customThe solvent is evaporated
  5. customAfter decanting
  6. extractionthe aqueous phase is again extracted with diethyl ether (450 cc)
  7. washThe combined organic phases are washed with an 8% (w/v) sodium bicarbonate solution (120 cc)
  8. dry with materialThey are dried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0ff1b009c45f40f2ba084a3b6d9e3f30
Source dataset
uspto-grants-1979_03
Patent number
US04144339

Reaction notes

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