Isothiocyanatotrimethylsilane → Ethyl 2-(6-(2,4-dimethoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)acetate

HRID 77556ノート

反応式

HRID 77556 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1/[C:11](/[NH:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12]/[C:13]([O:15]C)=O.C[Si]([N:28]=[C:29]=[S:30])(C)C.CCCCCCC.CCOC(C)=O>CC1CCCO1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:29](=[S:30])[NH:28][C:13](=[O:15])[CH:12]=1

参加物

5

反応物 3

HCID 75297IsothiocyanatotrimethylsilaneHCID 21899848Ethylacetate heptaneHCID 86684695(Z)-Methyl 3-(2,4-dimethoxyphenyl)-3-((2-ethoxy-2-oxoethyl)amino)acrylate

生成物 1

HCID 86684696Ethyl 2-(6-(2,4-dimethoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)acetate

試薬・触媒・溶媒 1

HCID 73012-Methyltetrahydrofuran溶媒

反応条件

温度
110 °C

実験手順

To a solution of (Z)-methyl 3-(2,4-dimethoxyphenyl)-3-((2-ethoxy-2-oxoethyl)amino)acrylate (4.68 g, 15.1 mmol) in 2-methyltetrahydrofuran (38 mL) was added (trimethylsilyl)isothiocyanate (12.9 mL, 90.8 mmol). The resulting solution was purged with nitrogen gas for 3 times, and the mixture was heated at 110° C. for 18 hours. The mixture was cooled down to room temperature and the solvent was removed under reduced pressure to give a red solid. This residue was suspended in a mixture of 3:1 heptane/EtOAc (200 mL), and it was stirred at room temperature for 1 hour. The solid was filtered, and triturated with CH2Cl2 (100 mL), concentrated under reduced pressure and dried under vacuum the title compound (4.42 g, 87%) as a pink solid. This material was used without further purification in the next step.

後処理

  1. customThe resulting solution was purged with nitrogen gas for 3 times
  2. temperatureThe mixture was cooled down to room temperature
  3. customthe solvent was removed under reduced pressure
  4. customto give a red solid
  5. filtrationThe solid was filtered
  6. customtriturated with CH2Cl2 (100 mL)
  7. concentrationconcentrated under reduced pressure
  8. dry with materialdried under vacuum the title compound (4.42 g, 87%) as a pink solid
  9. customThis material was used without further purification in the next step

出典と根拠

ORDレコード
ord-b42e9ebbaf154f98b155228965c30413
出典データセット
uspto-grants-2014_09
特許番号
US08841314B2

反応ノート

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