Potassium Carbonate → HCID 57839072, Verbindung

HRID 732955

Reaktionsgleichung

Reaktionsgleichung von HRID 732955
Cl[C:2]1[C:7]([CH:8]=[O:9])=C[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.[Cl:16][C:17]1[CH:18]=[C:19](B(O)O)[C:20]([CH3:23])=[CH:21][CH:22]=1.[C:27]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:7]([CH:8]=[O:9])=[CH:2][N:3]=[C:4]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:5]=2)=[C:19]([CH3:27])[CH:18]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 2773336(5-Chloro-2-methylphenyl)boronic acidHCID 57839061HCID 57839061, Verbindung

Produkt 1

HCID 57839072HCID 57839072, VerbindungAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a stirred solution of 4-chloro-2-phenylpyrimidine-5-carbaldehyde (50 mg, 0.23 mmol) and 4-chloro-o-toluene boronic acid (48 mg, 0.29 mmol) in dioxane (1 mL) and H2O (0.5 mL) was added Pd(PPh3)4 (26.5 mg, 0.02 mmol), K2CO3 (126.5 mg, 0.92 mmol). The reaction was heated to 85° C. for 6 hrs. After concentration under reduced pressure, the residue was diluted with EtOAc (10 mL) and the organic layer was washed with saturated NH4Cl solution (10 mL), and brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give the crude product (70 mg). The crude product was purified by flash chromatography (silica gel, 20% EtOAc/hexane) to give 4-(4-chloro-2-methylphenyl)-2-phenylpyrimidine-5-carbaldehyde (63 mg, 75%) as a white solid.

Aufarbeitung

  1. concentrationAfter concentration under reduced pressure
  2. additionthe residue was diluted with EtOAc (10 mL)
  3. washthe organic layer was washed with saturated NH4Cl solution (10 mL), and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product (70 mg)
  8. customThe crude product was purified by flash chromatography (silica gel, 20% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d8a06cc992f54305bf7417ba9ab58325
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589088B2

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