Methyl pyruvate → 2-Phenylpyrimidine-4-carboxylic acid

HRID 1045672Notes

Reaction equation

HRID 1045672 reaction equation
[C:1]([O:6]C)(=[O:5])[C:2]([CH3:4])=O.[CH3:8]OC(OC)N(C)C.Cl.[C:17]([NH2:25])(=[NH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C[O-].[Na+]>O.C(OCC)(=O)C>[C:18]1([C:17]2[N:25]=[C:2]([C:1]([OH:6])=[O:5])[CH:4]=[CH:8][N:24]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 11748Methyl pyruvateHCID 78373Dimethylformamide dimethyl acetalHCID 80289Benzamidine, hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 217091412-Phenylpyrimidine-4-carboxylic acidYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl pyruvate (5.61 g, 55.0 mmol) and dimethylformamide dimethylacetal (6.86 g, 57.6 mmol) was stirred for 2 hours at 80° C., and benzamidine hydrochloride (9.58 g, 61.2 mmol), sodium methoxide (28% in methanol, 23.1 g, 120 mmol) was added to the solution. After reflux for 3 hours, water was added and the organic solvents were removed under reduced pressure. Resulting solids were dissolved in a mixture of water and ethyl acetate, and the remaining insolubles were filtered off. The filtrate was acidified with hydrochloric acid, and extract with 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 dissolved in a mixture of ethanol and aqueous sodium hydroxide to treat with charcoal. After removal of charcoal, the filtrate was acidified with hydrochloric acid, and the removal of ethanol under reduced pressure followed by filtration and dryness afforded 2-phenyl-pyrimidine-4-carboxylic acid (2.51 g, 23%).

Workup

  1. temperatureAfter reflux for 3 hours
  2. customthe organic solvents were removed under reduced pressure
  3. customResulting solids
  4. filtrationthe remaining insolubles were filtered off
  5. extractionextract with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. dissolutionthe residue was dissolved in a mixture of ethanol and aqueous sodium hydroxide
  10. additionto treat with charcoal
  11. customAfter removal of charcoal
  12. customthe removal of ethanol under reduced pressure
  13. filtrationfollowed by filtration and dryness

Sources & evidence

ORD record
ord-68fc7cca025449c88ed74cb83f4721de
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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