Nitrogen → 4-(Methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidine

HRID 1465033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465033
Br[C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([S:11][CH3:12])[C:5]=2[S:4][CH:3]=1.C1(NC2CCCCC2)CCCCC1.[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])#[CH:27].N#N>C(#N)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.[Cu]I>[CH3:12][S:11][C:10]1[C:5]2[S:4][CH:3]=[C:2]([C:27]#[C:26][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:6]=2[N:7]=[CH:8][N:9]=1

Komponenten

8

Edukt 4

HCID 947NitrogenHCID 7582DicyclohexylamineHCID 66111TrimethylsilylacetyleneHCID 469284277-Bromo-4-methylsulfanylthieno[3,2-d]pyrimidine

Produkt 1

HCID 673274394-(Methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidineAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

7-Bromo-4-(methylthio)thieno[3,2-d]pyrimidine (3 g, 11.49 mmol) was dissolved in acetonitrile (30 mL) and then bis(triphenylphosphine)palladium(II) dichloride (204 mg, 0.29 mmol), CuI (76 mg, 0.40 mmol), dicyclohexylamine (2.5 mL, 12.64 mmol) and ethynyltrimethylsilane (3.2 mL, 22.98 mmol) were added thereto. The reaction mixture was treated with N2 gas for 15 minutes and stirred at 80° C. for 14 hours. The reaction mixture was cooled to room temperature, filtered using Celite and washed with ethyl acetate (50 mL). The filtrate was washed with brine and concentrated by drying with MgSO4. The resulting mixture was purified by silica gel chromatography (ethyl acetate/hexane=1:9˜2:8) to obtain the title compound (2.1 g, 65% yield) as a yellowish solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washwashed with ethyl acetate (50 mL)
  4. washThe filtrate was washed with brine
  5. concentrationconcentrated
  6. dry with materialby drying with MgSO4
  7. customThe resulting mixture was purified by silica gel chromatography (ethyl acetate/hexane=1:9˜2:8)

Quellen und Nachweise

ORD-Eintrag
ord-a36e33a791074d14a69a0490b9d346bd
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999973B2

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