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

HRID 12290

반응식

HRID 12290 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 5946Tetraethylammonium Chloride촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2c8b3ade3271450f9aea1bf3410a9b3b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727989B2

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