Potassium Carbonate → 1-cyclopentyl-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 238010Notes

Reaction equation

HRID 238010 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[N:16][C:17]=3[NH2:19])[NH:12][N:11]=2)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].I[CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>CN(C=O)C>[CH:27]1([N:12]2[C:13]3=[N:14][CH:15]=[N:16][C:17]([NH2:19])=[C:18]3[C:10]([C:4]3[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([F:1])[CH:3]=3)=[N:11]2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73784IodocyclopentaneHCID 178492931HCID 178492931, compound

Product 1

HCID 687128991-cyclopentyl-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA75, 100 mg, 0.386 mmol) was dissolved in DMF (10 ml). K2CO3 (250 mg, 1.54 mmol) was added and reaction was stirred at room temperature under an argon atmosphere. Iodocyclopentane (0.134 ml, 1.16 mmol) was added with a syringe and reaction was stirred 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 by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA79.

Workup

  1. customreaction
  2. customreaction
  3. stirringwas stirred for 2 hours
  4. customSolid K2CO3 was removed by filtration
  5. customSolvent was partially removed in vacuo
  6. additionSodium citrate (50 ml) was added
  7. customreaction
  8. extractionwas extracted with EtOAc
  9. concentrationOrganic phases concentrated in vacuo
  10. custompurified
  11. customto yield BA79

Sources & evidence

ORD record
ord-72a5b2157406494fad0a968383749c43
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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