Sodium Carbonate → 2,4-Dimethoxy-5-pyrazin-2-yl-pyrimidine

HRID 12743

Reaktionsgleichung

Reaktionsgleichung von HRID 12743
[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.I[C:15]1[CH:20]=[N:19][CH:18]=[CH:17][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]=[N:19][CH:18]=[CH:17][N:16]=2)=[CH:5][N:4]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 642841IodopyrazineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

Produkt 1

HCID 589942062,4-Dimethoxy-5-pyrazin-2-yl-pyrimidineAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

2,4-Dimethoxy-pyrimidine-5-boronic acid (1.33 g, 7.27 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-iodo-pyrazine (1.0 g, 4.85 mmol), Na2CO3 (1.02 g, 9.70 mmol), PPh3 (127 mg, 0.48 mmol) and Pd(OAc)2 (54 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography eluting with DCM-MeOH—NH4OH (99-1-0.1) to give 481 mg of the title compound (45% yield).

Aufarbeitung

  1. temperatureat reflux for 4 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
  6. customThe crude was purified by flash chromatography
  7. washeluting with DCM-MeOH—NH4OH (99-1-0.1)

Quellen und Nachweise

ORD-Eintrag
ord-d9b136ad99c54c0f9e509de38773057c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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