Bromocyclopentane → HCID 19432788, compound

HRID 1736573Notes

Reaction equation

HRID 1736573 reaction equation
[H-].[Na+].[C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[N:11][C:12]=2[NH2:14])[NH:7][N:6]=1)#[N:4].[CH:21]1(Br)[CH2:25][CH2:24][CH2:23][CH2:22]1>CN(C=O)C>[CH:21]1([N:7]2[C:8]3=[N:9][C:10]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)=[N:11][C:12]([NH2:14])=[C:13]3[C:5]([C:3]#[N:4])=[N:6]2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 178510689HCID 178510689, compound

Product 1

HCID 19432788HCID 19432788, compoundYield 7.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 97% NaH (0.64 g, 0.026 mol) in DMF (75 ml) was added 3-cyano-6-(4-pyridyl)-pyrazolo [3,4-d]pyrimidin-4amine (4.7 g, 0.02 mol). The reaction mixture was stirred at room temperature for 30 minutes then cyclopentyl bromide (3.1 g, 0.021 mol) in DMF (25 ml) was added dropwise. The reaction mixture was heated on a steam bath for 3 hours, cooled to room temperature and stirred for 24 hours. Inorganic salts were removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica eluting with ethyl acetate (100%) followed by preparative thin layer chromatography on silica eluting with ethyl acetate/hexanes (75/25) to afford 0.45 g (7%) of 1-cyclopentyl-3-cyano-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine, m.p. 219°-221° C. when recrystallized from ether and dried for 16 hours at 90° C. in high vacuum.

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for 3 hours
  2. temperaturecooled to room temperature
  3. stirringstirred for 24 hours
  4. customInorganic salts were removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography on silica eluting with ethyl acetate (100%)

Sources & evidence

ORD record
ord-ba6b7c3142b040789052f29ed80b6e5b
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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