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

HRID 1045673노트

반응식

HRID 1045673 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-26eebf93143842268c8112a5ff7decad
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569294B2

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