4-Aminopyridine → HCID 21104302, compound

HRID 1010833Notes

Reaction equation

HRID 1010833 reaction equation
[CH2:1]([N:5]1[C:9]2=[N:10][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])=[N:12][C:13](Cl)=[C:8]2[C:7]([CH3:22])=[N:6]1)[CH2:2][CH2:3][CH3:4].[NH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>COOCCOOC>[CH2:1]([N:5]1[C:9]2=[N:10][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])=[N:12][C:13]([NH:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[C:8]2[C:7]([CH3:22])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 17274-AminopyridineHCID 21104300HCID 21104300, compound

Product 1

HCID 21104302HCID 21104302, compoundYield 113.1%

Reagents, catalysts & solvents 1

HCID 20519614HCID 20519614, compoundSolvent

Procedure

1-Butyl-4-chloro-6-(2-fluoro-phenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine (100 mg, 0.31 mmole) and 4-aminopyridine (58 mg, 0.626 mmole) were combined in ethyleneglycol dimethoxy ether and heated to reflux for 4 hours. The reaction mixture was cooled and the product was isolated by filtration, washed with minimum cold solvent and dried to give 132 mg of product. 50 mg of this material was subjected to HPLC purification on reversed phase C18 column, eluting with gradient of water/acetonitrile/0.1% trifluoroacetic acid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe product was isolated by filtration
  5. washwashed with minimum cold solvent
  6. customdried

Sources & evidence

ORD record
ord-a89299e4308c437f8cf9a7987f248e73
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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