Methanol → Methyl 4,5-Diphenyl-pyrimidine-2-carboxylate

HRID 12572

Reaktionsgleichung

Reaktionsgleichung von HRID 12572
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][N:3]=1.[C:20]([O-:23])(=[O:22])C.[Na+].[CH3:25]O>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:8]1([C:6]2[C:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:4][N:3]=[C:2]([C:20]([O:23][CH3:25])=[O:22])[N:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

7

Edukt 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 126742762-Chloro-4,5-diphenylpyrimidine

Produkt 1

HCID 59338828Methyl 4,5-Diphenyl-pyrimidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A solution of 2-chloro-4,5-diphenyl-pyrimidine (107, 203 mg, 0.76 mmol) and sodium acetate (188 mg, 2.21 mmol) in MeOH (6 ml) and THF (2 ml) was degassed under argon for 10 min. Pd(OAc)2 (2.1 mg) and DPPF (13 mg) were added and CO (g) was bubbled through the solution. The reaction was heated to 110° C. in a sealed tube for 2 days. The solvent was removed in vacuo and the crude product was purified by column chromatography (10% ethyl acetate in hexane) to get the title compound.

Aufarbeitung

  1. customCO (g) was bubbled through the solution
  2. customThe solvent was removed in vacuo
  3. customthe crude product was purified by column chromatography (10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9bea9c85f39b4b5ab7219d457a1b1a99
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728014B2

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