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

HRID 12290
Notes
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Reaction equation

HRID 12290 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 5946
Tetraethylammonium Chloride
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2c8b3ade3271450f9aea1bf3410a9b3b
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07727989B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes