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

HRID 1482495

Reaktionsgleichung

Reaktionsgleichung von HRID 1482495
[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-one

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 CC under nitrogen. The solution was stirred at −78° C. for 3.5 hours, and then quenched with satd aq NH2Cl, 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 NH2Cl
  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-d40aaadb862d4059abe3fab291e05307
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09415055B2

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