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

HRID 409038Notes

Reaction equation

HRID 409038 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)C=O.O>[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

5

Reactant 2

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

Product 1

HCID 178508725HCID 178508725, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1H-pyrazolo[3,4-d]pyrimidin-4-amine (150 g, 1.11 mol, 1.00 equiv) and N-iodo-succinimide (375 g, 1.67 mol, 1.58 equiv) in N,N-dimethylformamide (2.5 L) was stirred at 80° C. for 5 h. The reaction mixture was cooled to room temperature and then diluted with 10 L of water. The solid was collected by filtration, washed with 2×1 L of saturated aqueous sodium sulfite and dried under vacuum to give 150 g (52%) of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid was collected by filtration
  3. washwashed with 2×1 L of saturated aqueous sodium sulfite
  4. customdried under vacuum

Sources & evidence

ORD record
ord-96cd63e64bbc4ddd8d79a2d5628d93e2
Source dataset
uspto-grants-2014_06
Patent number
US08759358B1

Reaction notes

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