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

HRID 589169

Reaktionsgleichung

Reaktionsgleichung von HRID 589169
[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 26 %

Versuchsvorschrift

To a stirred solution of 5-bromo-2-cyanopyrimidine (600 mg, 3.26 mmol) in THF (40 mL) at −78° C. was added methylmagnesium bromide (1.4M solution, 7 mL, 9.78 mmol). The reaction mixture was stirred for an additional 20 minutes until LC/MS analysis indicated that the reaction was complete. Quenching with saturated NH4Cl, extraction with EtOAc and drying over MgSO4, afforded the crude residue which was purified by flash column chromatography, gradient elution (0 to 50%) hexane/ethyl acetate, to afford compound Int-2a as a white solid (170 mg, 26% yield). HPLC-MS tR=0.54 min (UV254 nm); mass calculated for formula C6H5BrN2O 199.96, observed LCMS m/z 201.0 (M+H).

Aufarbeitung

  1. customQuenching with saturated NH4Cl, extraction with EtOAc
  2. dry with materialdrying over MgSO4
  3. customafforded the crude residue which
  4. customwas purified by flash column chromatography, gradient elution (0 to 50%) hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f16827ef7c29400dbd59ab2c26225c7d
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227971B2

Verknüpfte Notizen

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