Tetrahydrofuran → 1-(5-Bromopyrimidin-2-yl)ethan-1-one

HRID 1046102

Reaktionsgleichung

Reaktionsgleichung von HRID 1046102
[Br:1][C:2]1[CH:3]=[N:4][C:5](C#N)=[N:6][CH:7]=1.C[Mg+].[Br-].[CH2:13]1[CH2:17][O:16]CC1>>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:17](=[O:16])[CH3:13])=[N:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 6865465-Bromopyrimidine-2-carbonitrileHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 534880641-(5-Bromopyrimidin-2-yl)ethan-1-oneAusbeute 30,2 %

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 5-bromopyrimidine-2-carbonitrile (300 mg, 1.63 mmol) in THF (20 mL) was added MeMgBr (5.43 mL, 16.3 mmol) at −78° C. under nitrogen. The solution was stirred at −78° C. for 20 min., quenched with satd aq NH4Cl, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give an oil, which was purified by prep TLC (3:1 PE/EtOAc) to give 1-(5-bromopyrimidin-2-yl)ethanone (99 mg, yield 30.2%). 1H NMR (CDCl3): δ2.70 (s, 3H), 8.90 (m, 2H).

Aufarbeitung

  1. customquenched with satd aq NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto give an oil, which
  6. customwas purified by prep TLC (3:1 PE/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-d3727f56287c4a5085a760fc8f17c612
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569292B2

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