1,1'-Carbonyldiimidazole → 3-Oxo-3-(2-phenyl-pyrimidin-4-yl)-propionic acid ethyl ester

HRID 1045673Notes

Reaction equation

HRID 1045673 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13]([OH:15])=O)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1[CH:22]=[CH:21]N=C1)=O.C(O)(=O)[CH2:29][C:30]([OH:32])=[O:31].C([K])C.[Cl-].[Mg+2].[Cl-]>O1CCCC1>[CH2:21]([O:32][C:30](=[O:31])[CH2:29][C:13](=[O:15])[C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:12]=1)[CH3:22]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 5360315Magnesium ChlorideHCID 217091412-Phenylpyrimidine-4-carboxylic acidHCID 178461627HCID 178461627, compound

Product 1

HCID 578700193-Oxo-3-(2-phenyl-pyrimidin-4-yl)-propionic acid ethyl esterYield 58.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-phenyl-pyrimidine-4-carboxylic acid (3.49 g, 17.4 mmol) and 1,1′-carbonyldiimidazole (2.86 g, 17.7 mmol) in tetrahydrofuran (100 ml) was stirred at 60° C. for 20 min. After cooling to room temperature, ethyl potassium malonate (3.28 g, 19.2 mmol) and magnesium chloride (2.48 g, 26.1 mmol) were added and the solution was stirred at 60° C. for 7 hours. After removal of the solvent, hydrochloric acid was added to adjust pH to 4 to 2, and the resulting solution was partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified with silica gel column chromatography (eluent; hexane/ethyl acetate=2/1) to afford 3-oxo-3-(2-phenyl-pyrimidin-4-yl)-propionic acid ethyl ester (2.74 g, 58%).

Workup

  1. customAfter removal of the solvent, hydrochloric acid
  2. additionwas added
  3. customthe resulting solution was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (eluent; hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-26eebf93143842268c8112a5ff7decad
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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