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

HRID 589169ノート

反応式

HRID 589169 の反応式
[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

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 6865465-Bromopyrimidine-2-carbonitrileHCID 178418573HCID 178418573、化合物

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f16827ef7c29400dbd59ab2c26225c7d
出典データセット
uspto-grants-2016_01
特許番号
US09227971B2

反応ノート

読み込み中…