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

HRID 12733
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 12733
[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.[CH3:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1Br.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]>[CH3:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:6]1[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=1
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Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 8176303-Bromo-4-methylpyridineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

Produkt 1

HCID 589941505-(4-Methyl-pyridin-3-yl)-2,4-dimethoxy-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

2,4-Dimethoxypyrimidine-5-boronic acid (1.3 g, 7.23 mmol) was dissolved in degassed n-PrOH (20 ml) and then 4-methyl-3-bromo-pyridine (830 g, 4.82 mmol), Na2CO3 (1.02 g, 9.64 mmol), PPh3 (126 mg, 0.48 mmol) and Pd(OAc)2 (40 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 DCM. The organic phase was dried (Na2SO4) and evaporated to give the title compound that was used without further purification in the next step (quantitative yield).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a66b7a3b045043e6b8987f76f458da43
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07727988B2

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