Methyl pyruvate → 2-Phenylpyrimidine-4-carboxylic acid

HRID 1045672노트

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HRID 1045672 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 217091412-Phenylpyrimidine-4-carboxylic acid수율 23%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-68fc7cca025449c88ed74cb83f4721de
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569294B2

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