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

HRID 243314Notes

Reaction equation

HRID 243314 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=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

4

Reactant 2

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

Product 1

HCID 178508725HCID 178508725, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (5.0 g, 37 mmol) and NIS (10.7 g, 45 mmol) in DMF (100 mL) was stirred at 70° C. overnight. Then the mixture was cooled to room temperature and filtered to give 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (4.1 g) as a white solid. The filtrate was concentrated and the residue was treated with 10% Na2SO3 and filtered to give another batch. (5.1 g, 96% of total yield)

Workup

  1. temperatureThen the mixture was cooled to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-8baa4573c9b44eba866eae24209da686
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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