Isopropyl iodide → 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1910000Notes

Reaction equation

HRID 1910000 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-].[Cs+].[Cs+].I[CH:19]([CH3:21])[CH3:20].CCOC(C)=O>CN(C)C=O>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:19]([CH3:21])[CH3:20])[N:3]=1

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 178508725HCID 178508725, compound

Product 1

HCID 249053373-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 68.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (200 mg, 0.766 mmol) in N,N-Dimethylformamide (DMF) (5 mL) was added cesium carbonate (300 mg, 0.919 mmol) followed by 2-iodopropane (0.080 mL, 0.805 mmol), and the reaction mixture was stirred over the weekend (3 days) at 80° C. in a sealed vessel. The reaction was allowed to cool down to room temperature. The mixture was poured onto water and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated to afford 3-iodo-1-(1-methylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (160 mg) as a white solid. LC/MS (ES) m/z=3.4.0 [M+H]+.

Workup

  1. temperatureto cool down to room temperature
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-32aebbd122fc4940ad5a991a5797edf7
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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