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

HRID 1529958Notes

Reaction equation

HRID 1529958 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.C([O-])(O)=O.[Na+]>CN(C=O)C>[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

5

Reactant 3

HCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 120273N-IodosuccinimideHCID 516892Sodium Bicarbonate

Product 1

HCID 178508725HCID 178508725, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (3.0 g, 22.20 mmol, 1.0 eq) in DMF (30 mL), NIS (6.7 g, 24.42 mmol, 1.1 eq) was added at room temperature. The reaction mixture was stirred overnight at 60° C. The reaction mixture was cooled to room temperature and 10% aq. NaHCO3 (150 mL) was added to the reaction mixture. The solid was filtered and re-crystallization from DMF solvent to give 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (4.0 g, 69% in yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid was filtered
  3. customre-crystallization from DMF solvent

Sources & evidence

ORD record
ord-b853eaea088f4bc79689f1eb58125a54
Source dataset
uspto-grants-2015_07
Patent number
US09090621B2

Reaction notes

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