Chloroform → HCID 178489940, compound

HRID 516138Notes

Reaction equation

HRID 516138 reaction equation
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

Participants

8

Reactant 4

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

Product 1

HCID 178489940HCID 178489940, compoundYield 20.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-8ead94e28d294fa0a4274beef02de758
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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