1H-Pyrazolo[3,4-d]pyrimidin-4-amine → HCID 178508725, compound

HRID 1909999Notes

Reaction equation

HRID 1909999 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[N:8][C:9]([NH2:10])=[C:4]2[CH:3]=[N:2]1.C1C(=O)N([I:18])C(=O)C1>CN(C)C=O>[I:18][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:10])[NH:1][N:2]=1

Participants

4

Reactant 2

HCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 120273N-Iodosuccinimide

Product 1

HCID 178508725HCID 178508725, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1H-pyrazolo[3,4-d]pyrimidin-4-amine (1000 mg, 7.40 mmol) in N,N-Dimethylformamide (DMF) (30 mL) stirred under nitrogen at room temperature was added NIS (1998 mg, 8.88 mmol). The reaction mixture was stirred at 80° C. for 5 h. The reaction was allowed to cool to room temperature. The mixture was concentrated, and NH4OH solution (20 ml) and EtOH (20 ml) were added. The precipitated white solid was filtered and dried to give 1.24 g of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine. LC/MS (ES) m/z=261.9 [M+H]+.

Workup

  1. temperatureto cool to room temperature
  2. concentrationThe mixture was concentrated
  3. additionNH4OH solution (20 ml) and EtOH (20 ml) were added
  4. filtrationThe precipitated white solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-4c0875f298d3464fb12335f95325d85e
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

Loading…