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

HRID 883003노트

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HRID 883003 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 (1 L 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 (1 L silica, EtOAc)

출처 및 근거

ORD 기록
ord-2bbe4968b9ae4561a3fb232734526467
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236815B2

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