Water → Methyl 4-(4-pyrimidinyl)benzoate

HRID 379555노트

반응식

HRID 379555 반응식
[CH3:1][O:2]BO.Cl.Cl[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][N:8]=1.[F-].[K+].[OH2:15].[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[N:10]1[CH:11]=[CH:12][C:7]([C:19]2[CH:20]=[CH:21][C:16]([C:22]([O:2][CH3:1])=[O:15])=[CH:17][CH:18]=2)=[N:8][CH:9]=1

참가 물질

9

반응물 5

HCID 962WaterHCID 1140TolueneHCID 522689Potassium FluorideHCID 219225564-Chloropyrimidine hydrochlorideHCID 178486307HCID 178486307, 화합물

생성물 1

HCID 22329706Methyl 4-(4-pyrimidinyl)benzoate

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 8857Ethyl Acetate용매

실험 절차

1,1′-Bis(diphenylphosphino)ferrocene (2.48 g, 4.5 mmol) and palladium (II) acetate (1.0 g, 4.5 mmol) were stirred at 50° C. in toluene (25 ml) under an atmosphere of nitrogen for 30 minutes, then allowed to cool to room temperature. The boronic acid methyl ester from b) above (2.2 g, 11.2 mmol), 4-chloropyrimidine hydrochloride from a) above (1.69 g, 11.2 mmol) and potasium fluoride (3.9 g, 67 mmol) were added followed by water (25 mL). The reaction mixture was refluxed overnight under an atmosphere of nitrogen. The reaction mixture was separated between ethyl acetate (100 ml) and water (100 ml). The organic layer was dried over magnesium sulphate, filtered and concentrated in vacuo to yield a black oil which was subjected to chromatography (SiO2: 100% Ethyl acetate) to yield methyl 4-(4-pyrimidinyl)benzoate as a brown solid (1.17 g); 1H NMR (250 MHZ, DMSO-d6) δ=3.91 ppm (s,3H), δ8.13 & 8.36 ppm (dd,4H), δ=8.19 ppm (dd,1H), δ=8.94 ppm (d,1H), δ=9.32 ppm (d,1H); MS (M+H)+ 215.

후처리

  1. temperatureThe reaction mixture was refluxed overnight under an atmosphere of nitrogen
  2. customThe reaction mixture was separated between ethyl acetate (100 ml) and water (100 ml)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a black oil which

출처 및 근거

ORD 기록
ord-fc7cf8e88c524f8aa6f504e85c9be462
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300330B1

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