Cesium carbonate → 2-(2-Methoxy-4-nitrophenoxy)pyrimidine

HRID 38244

Reaktionsgleichung

Reaktionsgleichung von HRID 38244
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][O:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[OH:19].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[O:19][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 767382-Methoxy-4-nitrophenolHCID 783452-Bromopyrimidine

Produkt 1

HCID 674400092-(2-Methoxy-4-nitrophenoxy)pyrimidineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

According to Scheme 3 Step 1 Method B: 2-Bromopyrimidine (1.26 mmol, 211 mg) was added to a suspension of 2-methoxy-4-nitrophenol (1.15 mmol, 200 mg), Cs2CO3 (1.41 mmol, 460 mg) in DMF (3 mL). The reaction mixture was stirred at 80° C. for 3 days. The reaction mixture was quenched with water. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was washed with a solution of NaOH 3M and dried to obtain 2-(2-methoxy-4-nitrophenoxy)pyrimidine (0.89 mmol, 220 mg, 78%) as a solid. The product was used without further purification.

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. washThe crude product was washed with a solution of NaOH 3M
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-253ba729488a49fd979764e8aac6fb34
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524726B2

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