Sodium Carbonate → 5-(6-Fluoro-pyridin-2-yl)-2,4-dimethoxy-pyrimidine

HRID 12703

Reaktionsgleichung

Reaktionsgleichung von HRID 12703
[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]([F: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]>[F:21][C:17]1[N:16]=[C:15]([C:6]2[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)[CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 6394382-Bromo-6-fluoropyridineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

Produkt 1

HCID 589942165-(6-Fluoro-pyridin-2-yl)-2,4-dimethoxy-pyrimidineAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

2,4-Dimethoxy-pyrimidine-5-boronic acid (966 mg, 5.3 mmol) was dissolved in degassed n-PrOH (60 ml) and then 2-bromo-6-fluoropyridine (850 mg, 4.8 mmol), Na2CO3 (1.676 g, 15.8 mmol), PPh3 (400 mg, 1.52 mmol) and Pd(OAc)2 (116 mg) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was triturated with iPrOH to give 650 mg of the title compound as a white powder (52% yield).

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was triturated with iPrOH

Quellen und Nachweise

ORD-Eintrag
ord-f8171c7006b0492aa5e0fccdfb9481a4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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