Phenylboronic Acid → Methyl 2-(methylthio)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate

HRID 518783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 518783
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9](OS(C(F)(F)F)(=O)=O)[C:7]=2[N:8]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C>Cl[Pd]Cl.O1CCOCC1>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:7]=2[N:8]=1

Komponenten

6

Edukt 3

HCID 66827Phenylboronic AcidHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 86697952HCID 86697952, Verbindung

Produkt 1

HCID 86697951Methyl 2-(methylthio)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylateAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium ChlorideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Anhydrous dioxane is added, under argon, to a mixture of 2.5 g of methyl 2-(methylsulfanyl)-7-{[(trifluoromethyl)sulfonyl]oxy}thieno[3,2-d]pyrimidine-6-carboxylate 4 (example 1) and 0.785 g of phenylboronic acid. After the addition of 250 mg of dichloropalladium (dppf) and 4.09 g of BTPP, the mixture is refluxed for 20 h, and then cooled to ambient temperature. The mixture is filtered on silica gel, elution being carried out with ethyl acetate. The solvent is evaporated off under vacuum and the residue is triturated with an ethyl acetate/heptane mixture so as to obtain 1.6 g of methyl 2-(methylsulfanyl)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate in the form of a whitish precipitate.

Aufarbeitung

  1. temperaturethe mixture is refluxed for 20 h
  2. filtrationThe mixture is filtered on silica gel, elution
  3. customThe solvent is evaporated off under vacuum
  4. customthe residue is triturated with an ethyl acetate/heptane mixture so as

Quellen und Nachweise

ORD-Eintrag
ord-1ab7a8cf87c04e34a5341b129eba1404
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115140B2

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