Trimethylsilylacetylene → 2-Methyl-5-((trimethylsilyl)ethynyl)pyrimidine

HRID 1669664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669664
Br[C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.[CH3:9][Si:10]([C:13]#[CH:14])([CH3:12])[CH3:11]>CCN(CC)CC.C1COCC1.[Cu]I.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>[CH3:8][C:5]1[N:4]=[CH:3][C:2]([C:14]#[C:13][Si:10]([CH3:12])([CH3:11])[CH3:9])=[CH:7][N:6]=1

Komponenten

7

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 143877445-Bromo-2-methylpyrimidine

Produkt 1

HCID 668490422-Methyl-5-((trimethylsilyl)ethynyl)pyrimidineAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

5-Bromo-2-methyl-pyrimidine (prepared according to UK patent application GB 2 157 288) (0.2 g, 1.16 mmol), (trimethylsilyl)acetylene (164 μL, 1.3 mmol), CuI (0.022 g, 0.116 mmol) and PdCl2(PPh3)2 (0.082 g, 0.116 mmol) in Et3N (2 mL) and THF (2 mL) were stirred at 80° C. for 4 h. After cooling, the solvents were removed under vacuum and the residue chromatographed to give the subtitle compound (0.16 g, 50%).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solvents were removed under vacuum
  3. customthe residue chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-c38046dff2b84bc6845749fbd42f3708
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989620B2

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