Dichloromethane → HCID 69103390、化合物

HRID 2217254ノート

反応式

HRID 2217254 の反応式
[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1Br.[C:25]([Si:27]([CH3:30])([CH3:29])[CH3:28])#[CH:26].C(Cl)Cl.CCN(CC)CC>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.[Cu]I.CCOC(C)=O.O>[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1[C:26]#[C:25][Si:27]([CH3:30])([CH3:29])[CH3:28]

参加物

9

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 11429076HCID 11429076、化合物

生成物 1

HCID 69103390HCID 69103390、化合物収率 71.4%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

To a mixture of 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (500 mg), ethynyl(trimethyl)silane (255 mg), PdCl2(PPh3)2 (46 mg), CuI (12 mg), and CH2Cl2 (10 ml), was added NEt3 (0.2 ml) under ice-bath cooling. The mixture was allowed to warm to 25° C. and stirred for 15 hours. Water and EtOAc were poured into the mixture, and the organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by column chromatography (silica-gel; CH2Cl2—MeOH), recrystallized from EtOH, and dried in vacuo to give 5-{5-amino-3-phenyl-6-[(trimethylsilyl)ethynyl]-2-pyrazinyl}-1-isopropyl-2(1H)-pyridone (373 mg).

後処理

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography (silica-gel; CH2Cl2—MeOH)
  7. customrecrystallized from EtOH
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-3d6bc959d90647bd96d831f161d486d0
出典データセット
uspto-grants-2008_08
特許番号
US07407961B2

反応ノート

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