Ethanol → 5-(4-Formylphenyl)pyrimidine

HRID 50560

Reaktionsgleichung

Reaktionsgleichung von HRID 50560
C([O-])([O-])=O.[Na+].[Na+].C(O)C.Cl.Cl[C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[N:14]1[CH:13]=[C:12]([C:23]2[CH:24]=[CH:25][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=2)[CH:17]=[N:16][CH:15]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 227351705-Chloropyrimidine hydrochloride

Produkt 1

HCID 38612125-(4-Formylphenyl)pyrimidineAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)KatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1 M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of 5-chloropyrimidine hydrochloride (3.03 g, 20.06 mmol, prepared as described in WO 9821188), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.80 g (42%) of the title compound. MS 185 (M+H)+.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe cooled reaction mixture
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 4:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ae4430c86d0f46dba2137ba2e4b21c4e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713455B2

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