Hydrogen iodide → 4-Iodo-7H-pyrrolo(2,3-d)pyrimidine

HRID 1506110Notes

Reaction equation

HRID 1506110 reaction equation
[IH:1].Cl[C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1>>[I:1][C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 24841Hydrogen iodideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 578708044-Iodo-7H-pyrrolo(2,3-d)pyrimidineYield 96%

Conditions

Temperature
0 °C

Procedure

Hydroiodic acid (55 wt %, 100 g) was mixed with 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (manufactured by Tokyo Chemical Industry Co., Ltd., 10.6 g, 69.0 mmol) under cooling with ice and stirred at 0° C. for 1 hour and then at room temperature for one day. The precipitated solid was collected by filtration and washed with water. The residue was suspended in water, neutralized with 1 M aqueous sodium hydroxide and filtered. The yellow solid was washed with water and dried under reduced pressure to give the title compound as a yellow solid (16.2 g, yield 96%, including 10% 4-chloro-7H-pyrrolo[2,3-d]pyrimidine as the starting compound).

Workup

  1. temperatureunder cooling with ice
  2. waitat room temperature for one day
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. filtrationfiltered
  6. washThe yellow solid was washed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-70731825b7e1454280d0d6755c5e076b
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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