Potassium Carbonate → 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 238011

Reaction equation

HRID 238011 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C=O)C>[CH:19]1([N:4]2[C:5]3=[N:6][CH:7]=[N:8][C:9]([NH2:11])=[C:10]3[C:2]([I:1])=[N:3]2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73784IodocyclopentaneHCID 178508725HCID 178508725, compound

Product 1

HCID 223468081-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (400 mg, 1.53 mmol) and K2CO3 (1 g, 6 mmol) in DMF (5 ml) was stirred at room temperature under an argon atomosphere. Iodocyclopentane (1.0 g, 0.0084 mol) was added with a syringe. Reaction was refluxed under argon atmosphere for 2 hours. Solid K2CO3 was removed by filtration. Solvent was partially removed in vacuo. Sodium citrate (50 ml) was added and reaction was extracted with EtOAc. Organic phases concentrated in vacuo and purified using silica gel column chromatography [MeOH—CH2Cl2, 5:95] yielding BA80 (300 mg, 60% yield). ESI-MS (M+H)+ m/z calcd 330.0, found 330.0.

Workup

  1. customReaction
  2. temperaturewas refluxed under argon atmosphere for 2 hours
  3. customSolid K2CO3 was removed by filtration
  4. customSolvent was partially removed in vacuo
  5. additionSodium citrate (50 ml) was added
  6. customreaction
  7. extractionwas extracted with EtOAc
  8. concentrationOrganic phases concentrated in vacuo
  9. custompurified
  10. customyielding BA80 (300 mg, 60% yield)

Sources & evidence

ORD record
ord-99fa0499fb4c4f1494e05ecd28b77800
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Linked notes

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