Hydrochloric Acid → Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoate

HRID 1671486Notes

Reaction equation

HRID 1671486 reaction equation
CCC([O-])(C)C.[K+].[N:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]CC)=O)=[N:10][CH:9]=1.Cl.[C:20]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:21]>C1(C)C=CC=CC=1.O>[O:16]=[C:14]([C:11]1[CH:12]=[CH:13][N:8]=[CH:9][N:10]=1)[CH2:21][C:20]([O:23][CH2:24][CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 13639438Ethyl pyrimidine-4-carboxylateHCID 23683543Potassium t-amylate

Product 1

HCID 11961458Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoateYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a 25% solution (5.31 g, 10.52 mmol) of potassium tert-amylate in toluene was added dropwise a solution of ethyl pyrimidine-4-carboxylate (1.00 g, 6.57 mmol) and ethyl acetate (1.09 mL, 11.1 mmol) in toluene (2.4 ml) at room temperature. Disappearance of the ethyl ester was confirmed by HPLC analysis, water (5 mL), ethyl acetate (5 mL) and concentrated hydrochloric acid (0.45 mL) were added, and the mixture was extracted with ethyl acetate (4 mL). The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give ethyl 3-oxo-3-(pyrimidin-4-yl)propionate (0.97 g, 76%).

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with ethyl acetate (4 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-47eb3ab4c6fe4406842fa3367c4dcd71
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Reaction notes

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