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

HRID 1485329Notes

Reaction equation

HRID 1485329 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.[I:11]N1C(=O)CCC1=O>CN(C=O)C>[I:11][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 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1H-Pyrazolo[3,4-d]pyrimidin-4-amine, 30 (5.0 g, 37 mmol, 1 equiv) was suspended in DMF (100 mL) and N-iodosuccinimide (NIS) (10.7 g, 45 mmol, 1.2 equiv) was added. The reaction was heated at 80° C. for 2 hours. The reaction was cooled to room temperature and then to 0° C. and was quenched by the drop-wise addition of water (200 mL). The resulting solids were collected by filtration, washed with water and cold ethanol, and dried in a vacuum oven to yield 31 (8.1 g, 84% yield) as a beige solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customto 0° C. and was quenched by the drop-wise addition of water (200 mL)
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with water and cold ethanol
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-8ef1d43504384b29a3cc45cba7bb505e
Source dataset
uspto-grants-2016_08
Patent number
US09422295B2

Reaction notes

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