Tetrabutylammonium Fluoride → 7-Ethynyl-4-(methylthio)thieno[3,2-d]pyrimidine

HRID 1465034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465034
[CH3:1][S:2][C:3]1[C:4]2[S:11][CH:10]=[C:9]([C:12]#[C:13][Si](C)(C)C)[C:5]=2[N:6]=[CH:7][N:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:12]([C:9]1[C:5]2[N:6]=[CH:7][N:8]=[C:3]([S:2][CH3:1])[C:4]=2[S:11][CH:10]=1)#[CH:13]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 673274394-(Methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidine

Produkt 1

HCID 866741357-Ethynyl-4-(methylthio)thieno[3,2-d]pyrimidineAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(Methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidine (500 mg, 1.8 mmol) was dissolved in THF (5 mL) at 1.0M and then tetrabutylammonium fluoride solution (3.6 mL, 3.6 mmol) was added thereto. The reaction mixture was stirred at room temperature for 30 minutes and then concentrated. The resulting mixture was purified by silica gel chromatography (ethyl acetate/hexane=2:8˜3:7) to obtain the title compound (340 mg, 91% yield) as a yellowish solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe resulting mixture was purified by silica gel chromatography (ethyl acetate/hexane=2:8˜3:7)

Quellen und Nachweise

ORD-Eintrag
ord-031fd6c366114e0e8991eb1c4ecf63f0
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999973B2

Notizen zur Reaktion

Wird geladen…