Sodium Carbonate → 5-(2-Chloro-5-fluoro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine

HRID 12699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12699
I[C:2]1[C:3]([O:10][CH3:11])=[N:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[Cl:12][C:13]1[C:18](B(O)O)=[CH:17][C:16]([F:22])=[CH:15][N:14]=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]>[Cl:12][C:13]1[C:18]([C:2]2[C:3]([O:10][CH3:11])=[N:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=2)=[CH:17][C:16]([F:22])=[CH:15][N:14]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2634165-Iodo-2,4-dimethoxypyrimidineHCID 249017742-Chloro-5-fluoropyridine-3-boronic acid

Produkt 1

HCID 589942395-(2-Chloro-5-fluoro-pyridin-3-yl)-2,4-dimethoxy-pyrimidineAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

5-Iodo-2,4-dimethoxy-pyrimidine (868 mg, 3.3 mmol) was dissolved in degassed n-PrOH (30 ml) and then 2-chloro-5-fluoropyridine-3-boronic acid (858 mg, 4.9 mmol), Na2CO3 (700 mg, 6.6 mmol), PPh3 (88 mg, 0.33 mmol) and Pd(OAc)2 (90 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between brine and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether 2-8 affording 240 mg of the title compound (27% yield).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-5d2ba8741cdc4601a6f678054ff65ceb
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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