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

HRID 883003ノート

反応式

HRID 883003 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 517045Sodium AcetateHCID 54124074HCID 54124074、化合物HCID 178513471HCID 178513471、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2bbe4968b9ae4561a3fb232734526467
出典データセット
uspto-grants-2012_08
特許番号
US08236815B2

反応ノート

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