Potassium Fluoride → 4-(1H-Benzimidazol-2-yl)-6-[2-methylsulfanyl pyrimidin-4-yl]-2H-pyridazin-3-one

HRID 12290

反応式

HRID 12290 の反応式
Cl[C:2]1[CH:3]=[C:4]([C:17]2[N:21](COCC[Si](C)(C)C)[C:20]3[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=3[N:18]=2)[C:5](=[O:16])[N:6](COCC[Si](C)(C)C)[N:7]=1.[CH3:34][S:35][C:36]1[N:41]=[C:40]([Sn](CCCC)(CCCC)CCCC)[CH:39]=[CH:38][N:37]=1.[F-].[K+]>[Cl-].C([N+](CC)(CC)CC)C.CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:21]1[C:20]2[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=2[N:18]=[C:17]1[C:4]1[C:5](=[O:16])[NH:6][N:7]=[C:2]([C:38]2[CH:39]=[CH:40][N:41]=[C:36]([S:35][CH3:34])[N:37]=2)[CH:3]=1

参加物

7

反応物 3

HCID 522689Potassium FluorideHCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidineHCID 686802706-chloro-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

生成物 1

HCID 1359788044-(1H-Benzimidazol-2-yl)-6-[2-methylsulfanyl pyrimidin-4-yl]-2H-pyridazin-3-one

試薬・触媒・溶媒 3

HCID 5946Tetraethylammonium Chloride触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

The compound is prepared in analogy to example 15. A Stille coupling is carried out instead of the Suzuki coupling. This entails dissolving 6-chloro-4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxy-methyl)-2H-pyridazin-3-one, 2-methylsulfanyl-4-tributylstannylpyrimidine, tetra-ethylammonium chloride and bis(triphenylphosphine)palladium(II) chloride in DMF under argon and heating at 80° C. for 6 hours. After cooling to room temperature, 30% aqueous potassium fluoride solution is added, and the mixture is stirred for 30 minutes. Extraction with ethyl acetate and drying on a drying column afford after purification on SiO2 4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-6-(2-methyisulfanylpyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one which is reacted further in analogy to example 15.

後処理

  1. customThe compound is prepared in analogy to example 15
  2. temperatureAfter cooling to room temperature
  3. extractionExtraction with ethyl acetate
  4. customdrying on a drying column
  5. customafford
  6. customafter purification on SiO2 4-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-6-(2-methyisulfanylpyrimidin-4-yl)-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one which
  7. customis reacted further in analogy to example 15

出典と根拠

ORDレコード
ord-2c8b3ade3271450f9aea1bf3410a9b3b
出典データセット
uspto-grants-2010_06
特許番号
US07727989B2

関連ノート

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