4-Aminopyridine → HCID 21104302, compound

HRID 1354302Notes

Reaction equation

HRID 1354302 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. Cooled reaction mixture and isolated product by filtration, washed with minimum cold solvent and dried to give 132 mg 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. temperatureCooled
  4. customreaction mixture
  5. customisolated product
  6. filtrationby filtration
  7. washwashed with minimum cold solvent
  8. customdried

Sources & evidence

ORD record
ord-e59bf7b882da4ed4ab3fc7c2731ca8c1
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

Loading…