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

HRID 514894

反応式

HRID 514894 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 61%

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-71a37e665ded4f3a9f8e1cbfe2daea43
出典データセット
uspto-grants-2015_08
特許番号
US09108938B2

関連ノート

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