Potassium Carbonate → HCID 68212423, compound

HRID 928240Notes

Reaction equation

HRID 928240 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])=[N:8][CH:9]=2)[NH:4][N:3]=1.[OH:16][CH:17]1[CH2:22][CH2:21][CH:20](Cl)[CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:16][CH:17]1[CH2:22][CH2:21][CH:20]([N:4]2[C:5]3=[N:6][C:7]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])=[N:8][CH:9]=[C:10]3[C:2]([Br:1])=[N:3]2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 346094-ChlorocyclohexanolHCID 178448853HCID 178448853, compound

Product 1

HCID 68212423HCID 68212423, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3-bromo-N-butyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine (122 mg, 0.45 mmol) and 4-hydroxy-cyclohexyl chloride (260 mg, 1.9 mmol) in DMF (6.0 mL) was added K2CO3 (270 g, 2.0 mmol). The mixture was heated at 150° C. for overnight. After the reaction was cooled to room temperature, the reaction was quenched with H2O. The reaction mixture was partitioned in H2O and EtOAc. The aqueous phase was extracted with EtOAc (3×). The combined organic phase were dried (Na2SO4) and concentrated. The residue was purified by Isco to provide a mixture of cis- and trans-1-(4-hydroxy-cyclohexyl)-3-bromo-N-butyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine (90 mg, 54%) as a yellow solid.

Workup

  1. temperatureAfter the reaction was cooled to room temperature
  2. customthe reaction was quenched with H2O
  3. customThe reaction mixture was partitioned in H2O
  4. extractionThe aqueous phase was extracted with EtOAc (3×)
  5. dry with materialThe combined organic phase were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by Isco
  8. customto provide

Sources & evidence

ORD record
ord-f57a7645d5404b8da9b7f6bc876fea74
Source dataset
uspto-grants-2016_03
Patent number
US09290499B2

Reaction notes

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