StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Chlorotrimethylsilane → HCID 86762582, Verbindung

HRID 2401194
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2401194
BrCCBr.C[Si](C)(C)Cl.[C:10]([O:18][CH2:19]I)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl:21][C:22]1[CH:27]=[C:26](Cl)[N:25]=[CH:24][N:23]=1>C1COCC1.[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]([O:18][CH2:19][C:26]1[CH:27]=[C:22]([Cl:21])[N:23]=[CH:24][N:25]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 709434,6-DichloropyrimidineHCID 10015543Iodomethyl Benzoate2×

Produkt 1

HCID 86762582HCID 86762582, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994
Zinc
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Zinc (4.81 g, 73.6 mmol) was suspended in THF (6 mL), treated with 1,2-dibromoethane (0.313 mL, 3.63 mmol) and the resulting mixture was heated at 60° C. under argon for 30 minutes. The reaction mixture was allowed to cool to room temperature, treated with trimethylchlorosilane (0.120 mL, 0.938 mmol) and the resulting mixture was stirred at room temperature for 30 minutes. A solution of iodomethyl benzoate (Intermediate 23, 3.15 g, 12.02 mmol) in THF (6 mL) was added and the resulting mixture was stirred at room temperature for 1 hour. This reaction mixture was added to a solution of 4,6-dichloropyrimidine (1.075 g, 7.21 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.695 g, 0.601 mmol) in THF (11 mL) and the resulting mixture was stirred at room temperature under argon for 18 hours. The reaction mixture was filtered through celite, diluted with saturated ammonium chloride solution and extracted with ethyl acetate (×2). The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-20% ethyl acetate and isohexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a yellow solid (394 mg);

Aufarbeitung

  1. temperatureto cool to room temperature
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour
  3. stirringthe resulting mixture was stirred at room temperature under argon for 18 hours
  4. filtrationThe reaction mixture was filtered through celite
  5. additiondiluted with saturated ammonium chloride solution
  6. extractionextracted with ethyl acetate (×2)
  7. customdried under magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography (Biotage SP4)
  10. washeluting with a gradient of 0-20% ethyl acetate and isohexane
  11. additionProduct containing fractions
  12. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6fe6fad2eb4f48868146112248a078a8
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08796283B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion