Sodium hydride → HCID 19432773, compound

HRID 487282Notes

Reaction equation

HRID 487282 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[H-].[Na+].[CH:20]1([CH2:25]Br)[CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C=O)C>[CH:20]1([CH2:25][N:4]2[C:5]3=[N:6][C:7]([C:12]4[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=4)=[N:8][C:9]([NH2:11])=[C:10]3[C:2]([CH3:1])=[N:3]2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12723264(Bromomethyl)cyclopentaneHCID 178434429HCID 178434429, compound

Product 1

HCID 19432773HCID 19432773, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine (6.0 g, 0.027 mol) in DMF (50 ml) at 0° C. was added 60% NaH/mineral oil dispersion (1.06 g, 0.027 mol) in one portion. The reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was cooled to 0° C. and cyclopentylmethyl bromide (4.3 g, 0.027 mol) was added dropwise over 5 minutes. The reaction mixture was warmed to room temperature and stirred for 50 hours. The solvent was removed in vacuo, the yellow slurry was added to water (100 ml) and acidified with acetic acid. The resulting paste was stripped to dryness and the residue was slurried with ethanol. A tan solid was collected by filtration and purified by column chromatography on silica eluting with ether/ethanol/water (97.5/2/0.5) followed by recrystallization from cyclohexane to afford 2.2 g (26%) of 1-cyclopentylmethyl-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d] -pyrimidin-4-amine, m.p. 177°-178° C.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperatureThe reaction mixture was warmed to room temperature
  3. stirringstirred for 50 hours
  4. customThe solvent was removed in vacuo
  5. additionthe yellow slurry was added to water (100 ml)
  6. filtrationA tan solid was collected by filtration
  7. custompurified by column chromatography on silica eluting with ether/ethanol/water (97.5/2/0.5)
  8. customfollowed by recrystallization from cyclohexane

Sources & evidence

ORD record
ord-c9e1b208b0aa4dbc895211a040126405
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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