Iodoethane → 1-ethyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1910007Notes

Reaction equation

HRID 1910007 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[CH2:19][CH3:20].CCOC(C)=O>CN(C)C=O>[CH2:19]([N:4]1[C:5]2=[N:6][CH:7]=[N:8][C:9]([NH2:11])=[C:10]2[C:2]([I:1])=[N:3]1)[CH3:20]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 178508725HCID 178508725, compound

Product 1

HCID 668236371-ethyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 51.9%

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 iodoethane (0.065 mL, 0.805 mmol), and the reaction mixture was stirred over the weekend (3 days) at 80° C. into 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. Flash chromatography on SiO2 (gradient: 100% CH2Cl2 to 90:10:1 CH2Cl2:CH3OH:NH4OH) afforded 1-ethyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (115 mg) as a white solid.

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-967e30d825334dff9ec24b5db96911c5
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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