Trimethylaluminum → 1-(1-Ethylpropyl)-5-methyl-3-(methylthio)-2 (1H)-pyrazinone

HRID 2251004ノート

反応式

HRID 2251004 の反応式
Br[C:2]1[N:3]=[C:4]([S:14][CH3:15])[C:5](=[O:13])[N:6]([CH:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:7]=1.[CH3:16][Al](C)C>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:9]([CH:8]([N:6]1[CH:7]=[C:2]([CH3:16])[N:3]=[C:4]([S:14][CH3:15])[C:5]1=[O:13])[CH2:11][CH3:12])[CH3:10]

参加物

5

反応物 2

HCID 16682925TrimethylaluminumHCID 588451705-bromo-1-(1-ethylpropyl)-3-(methylthio)-2 (1H)-pyrazinone

生成物 1

HCID 588451711-(1-Ethylpropyl)-5-methyl-3-(methylthio)-2 (1H)-pyrazinone収率 73%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of XXXI (2.0 g, 6.9 mmol) and dichlorobis(triphenylphosphine)palladium(II) (484 mg, 0.7 mmol) in THF (40 mL) was treated with trimethylaluminum (6.2 mL, 12.4 mmol, 2M/toluene) dropwise at 0° C. The reaction was refluxed for 4 h, cooled to 0° C. quenched with water (50 mL) and extracted with ethyl acetate (100 mL). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo to give crude residue. Purification by flash column chromatography (silica, ethyl acetate:hexane 1:1) gave the product XXXII (1.14 g, 73%) as a pale yellow solid.

後処理

  1. temperatureThe reaction was refluxed for 4 h
  2. customquenched with water (50 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give crude residue
  8. customPurification by flash column chromatography (silica, ethyl acetate:hexane 1:1)

出典と根拠

ORDレコード
ord-c231cc311fa8401ca9cd6ccdc073b0bb
出典データセット
uspto-grants-2008_01
特許番号
US07319100B2

反応ノート

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