Water → HCID 178508725, compound

HRID 432143Notes

Reaction equation

HRID 432143 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[I:11]N1C(=O)CCC1=O.O>CN(C)C=O>[I:11][C:10]1[C:3]2[C:4](=[N:5][CH:6]=[N:7][C:2]=2[NH2:1])[NH:8][N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 120273N-Iodosuccinimide2×

Product 1

HCID 178508725HCID 178508725, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-aminopyrazolo[3,4-d]pyrimidine (Intermediate KA) (11.75 g, 0.087 mol) and N-iodosuccinimide (25.45 g, 0.113 mol) in dimethylformamide (300 mL) was heated at 50° C. for 24 h. Additional N-iodosuccinimide (3.92 g, 0.017 mol) was added and heating at 50° C. was continued for another 24 h. The mixture was allowed to cool to ambient temperature and the volume was reduced by ⅓ under reduced pressure. Water (500 mL) was added to the resulting slurry to yield a dark brown precipitate which was collected by filtration, washed with water and ethanol and dried in vacuo to give 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine as a light yellow powder (97%, 22 g, 0.084 mol): 1H NMR (DMSO-d6, 400 MHz) 13.81 (s, 1H), 8.17 (s, 1H), 2.73 (s, 1H), 2.57 (s, 1H); TLC (dichloromethane/methanol=9:1) Rf 0.4.

Workup

  1. temperatureheating at 50° C.
  2. temperatureto cool to ambient temperature
  3. customto yield a dark brown precipitate which
  4. filtrationwas collected by filtration
  5. washwashed with water and ethanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9a739a1c784f4505a5caac41c5ae5759
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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