Chloroform → HCID 178489940, 화합물

HRID 516138노트

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HRID 516138 반응식
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

참가 물질

8

반응물 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 46613211-Ethynyl-3,5-dimethoxybenzeneHCID 178508725HCID 178508725, 화합물

생성물 1

HCID 178489940HCID 178489940, 화합물수율 20.4%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-8ead94e28d294fa0a4274beef02de758
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108973B2

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