Water → Ethyl 4-(2-fluorophenyl)-2-(methylthio)-5-pyrimidinecarboxylate

HRID 1036611노트

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HRID 1036611 반응식
[CH2:1]([O:3][C:4](=[O:19])[C:5]([C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=[CH:6]N(C)C)[CH3:2].S(O)(O)(=O)=O.[NH2:25][C:26](=[NH:28])[SH:27].[CH3:29]C([O-])=O.[Na+].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[N:28][C:26]([S:27][CH3:29])=[N:25][CH:6]=1)=[O:19])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 517045Sodium AcetateHCID 54124074HCID 54124074, 화합물HCID 178513471HCID 178513471, 화합물

생성물 1

HCID 59421256Ethyl 4-(2-fluorophenyl)-2-(methylthio)-5-pyrimidinecarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

3-Dimethylamino-2-(2-fluoro-benzoyl)-acrylic acid ethyl ester was dissolved in DMF (100 mL). To the solution was added isothiourea sulfate (18.92 g, 68.0 mmol) and NaOAc (23.24 g, 0.28 mol). The reaction mixture was heated at 80-90° C. overnight. Water was added to the cooled solution. The product was extracted with EtOAc (3×100 mL). The combined organic layers were washed with a saturated aqueous NaHCO3 solution and water, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography OL silica, EtOAc) to give 4-(2-fluoro-phenyl)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester as a yellow oil (11.86 g, 40.6 mmol, 60% over 2 steps).

후처리

  1. extractionThe product was extracted with EtOAc (3×100 mL)
  2. washThe combined organic layers were washed with a saturated aqueous NaHCO3 solution and water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography OL silica, EtOAc)

출처 및 근거

ORD 기록
ord-4d1905e1a4fc4501ba55603529274320
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546414B2

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