Chloroform → HCID 178489940、化合物

HRID 516138ノート

反応式

HRID 516138 の反応式
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[C:12]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[CH:15]=1)#[CH:13].C(N(CC)CC)C.C(Cl)(Cl)Cl>CN(C=O)C.[Cu]I.O>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([C:12]#[C:13][C:2]2[C:10]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH2:11])[NH:4][N:3]=2)[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=1

参加物

8

反応物 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 46613211-Ethynyl-3,5-dimethoxybenzeneHCID 178508725HCID 178508725、化合物

生成物 1

HCID 178489940HCID 178489940、化合物収率 20.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

PdCl2(dppf)CH2Cl2 (163 mg) was added to a mixture of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (520 mg) synthesized by the method disclosed in WO 2007/126841, 1-ethynyl-3,5-dimethoxybenzene (504 mg), copper (I) iodide (57.3 mg), and triethylamine (0.56 ml) in DMF (10 ml). After nitrogen purging, the resulting mixture was stirred at 90° C. for 6 hours. Chloroform and water were added to the reaction mixture to separate the organic layer. After being washed with a saturated sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by basic silica gel column chromatography (developing solvent: chloroform/methanol) to obtain the title compound as a dark-brown solid (120 mg). Physical properties: m/z [M+H]+ 296.0

後処理

  1. customsynthesized by the method
  2. customto separate the organic layer
  3. washAfter being washed with a saturated sodium chloride solution
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customThe resulting residue was purified by basic silica gel column chromatography (developing solvent: chloroform/methanol)

出典と根拠

ORDレコード
ord-8ead94e28d294fa0a4274beef02de758
出典データセット
uspto-grants-2015_08
特許番号
US09108973B2

反応ノート

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