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

HRID 514894

Reaktionsgleichung

Reaktionsgleichung von HRID 514894
[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 178418573HCID 178418573, Verbindung

Produkt 1

HCID 534880641-(5-Bromopyrimidin-2-yl)ethan-1-oneAusbeute 61 %

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 5-bromopyrimidine-2-carbonitrile (221 mg, 1.2 mmol) in THF (10 ml) was added methylmagnesium bromide (3.0 ml, 4.20 mmol, 1.4 molar, THF) at −78° C. under nitrogen. The solution was stirred at −78° C. for 3.5 hours, and then quenched with satd aq NH4Cl, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated. The reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1) to afford 1-(5-bromopyrimidin-2-yl)ethanone (1.55 mg, 61% yield). 1H NMR (CDCl3 500 MHz): δ 9.00 (s, 2H), 2.80 (s, 3H).

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. customThe reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1)

Quellen und Nachweise

ORD-Eintrag
ord-71a37e665ded4f3a9f8e1cbfe2daea43
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108938B2

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