Dimethylformamide → HCID 22347118, compound

HRID 897867Notes

Reaction equation

HRID 897867 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[N:16]([C:24]3[CH:29]=[CH:28][C:27](Br)=[CH:26][N:25]=3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[H][H]>C(O)C.[Pd]>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[N:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[N:15]=2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 22347294HCID 22347294, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22347118HCID 22347118, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The more polar compound, 3-(4-phenoxyphenyl)-1-(5-bromo-2-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, was suspended in absolute ethanol (10 mL) and N,N-dimethylformamide (5 mL) and 10% palladium on carbon (0.007 g) was added. The mixture was stirred under a balloon atmosphere of hydrogen for 18 hours. The mixture was filtered through pad of Celite® 521, washing with absolute ethanol. The solvent was removed in vacuo to give 3-(4-phenoxyphenyl)-1-(2-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.030 g, 0.00007 mol) as a white solid.

Workup

  1. filtrationThe mixture was filtered through pad of Celite® 521
  2. washwashing with absolute ethanol
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fd4fdaa1fb024f31a0316e38a0d6369f
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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