Isopropanol → 2-Chloro-7-phenylthieno[3,2-d]pyrimidine

HRID 1615594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615594
Br[C:2]1[C:6]2[N:7]=[C:8]([Cl:11])[N:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:11][C:8]1[N:9]=[CH:10][C:5]2[S:4][CH:3]=[C:2]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Komponenten

7

Edukt 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 569657247-Bromo-2-chlorothieno(3,2-d)pyrimidine

Produkt 1

HCID 582288992-Chloro-7-phenylthieno[3,2-d]pyrimidineAusbeute 141,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 7-bromo-2-chlorothieno[3,2-d]pyrimidine (1.0 g, 4.0 mmol), phenyl boronic acid (0.6 g, 4.9 mmol), Pd[PPh3]4 (0.47 g, 0.4 mmol) and aqueous sodium carbonate (2M, 4.5 mL, 9.0 mmol) in toluene (25 mL)/isopropanol (8 mL) was heated under reflux overnight. The mixture was allowed to cool to room temperature, was diluted with ethyl acetate then washed with 10% aqueous sodium bicarbonate, dried (Na2SO4) filtered and concentrated. The resultant solid was sonicated in diethyl ether (2×70 mL) and the combined ether washes were evaporated to afford the crude product (1.4 g), still containing starting material and OPPh3.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. washthen washed with 10% aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant solid was sonicated in diethyl ether (2×70 mL)
  8. customthe combined ether washes were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1a584c265713426bba2a9c9fac3c58d2
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765755B2

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