Sodium Carbonate → 5-(2,4-Dimethyl-oxazol-5-yl)-2,4-dimethoxy-pyrimidine

HRID 12690

Reaktionsgleichung

Reaktionsgleichung von HRID 12690
[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[O:19][C:18]([CH3:20])=[N:17][C:16]=1[CH3:21].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]>[CH3:20][C:18]1[O:19][C:15]([C:6]2[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)=[C:16]([CH3:21])[N:17]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 593375895-Iodo-2,4-dimethyl-oxazole

Produkt 1

HCID 589942085-(2,4-Dimethyl-oxazol-5-yl)-2,4-dimethoxy-pyrimidineAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

2,4-Dimethoxy-pyrimidine-5-boronic acid (840 mg, 4.6 mmol) was dissolved in degassed n-PrOH (40 mL) and then 5-iodo-2,4-dimethyl-oxazole (Prep60, 850 mg, 3.8 mmol), Na2CO3 (848 mg, 8 mmol), PPh3 (332 mg, 1.3 mmol) and Pd(OAc)2 (85 mg, 0.38 mmol) 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 ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by SCX cartridge to give 600 mg of the title compound (66% yield).

Aufarbeitung

  1. temperatureat reflux for 4 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 purified by SCX cartridge

Quellen und Nachweise

ORD-Eintrag
ord-49aa7eb002944783b9f978f9c7b080b9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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