Sodium Carbonate → HCID 58994162, Verbindung

HRID 12681

Reaktionsgleichung

Reaktionsgleichung von HRID 12681
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](B(O)O)=[CH:5][N:4]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)=[CH:5][N:4]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 792052-Bromo-6-methylpyridineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

Produkt 1

HCID 58994162HCID 58994162, VerbindungAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

2,4-Di-methoxy-pyrimidine-5-boronic acid (500 mg, 2.72 mmol) was dissolved in degassed n-PrOH (40 mL) and then 2-bromo-6-methylpyridine (660 mg, 3.8 mmol), Na2CO3 (865 mg, 8.16 mmol), PPh3 (215 mg, 0.8 mmol) and Pd(OAc)2 (50 mg, 0.22 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated and the crude was partitioned between water and Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (2-8) to give 300 mg of the title compound (47% yield).

Aufarbeitung

  1. temperatureat reflux for 4 hours
  2. customThe solvent was evaporated
  3. customthe crude was partitioned between water and Et2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (2-8)

Quellen und Nachweise

ORD-Eintrag
ord-aee16765237f4c5d918624d6c4d3c6ad
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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