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

HRID 589169Notes

Reaction equation

HRID 589169 reaction equation
[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

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 6865465-Bromopyrimidine-2-carbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 534880641-(5-Bromopyrimidin-2-yl)ethan-1-oneYield 26%

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f16827ef7c29400dbd59ab2c26225c7d
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

Loading…