Sodium Hydroxide → 4-Chloro-6-iodo-7H-pyrrolo(2,3-d)pyrimidine

HRID 2375814Notes

Reaction equation

HRID 2375814 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([I:11])[N:8](S(C3C=CC=CC=3)(=O)=O)[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([I:11])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 574158854-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-D]pyrimidine

Product 1

HCID 457897324-Chloro-6-iodo-7H-pyrrolo(2,3-d)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-chloro-6-iodo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (538 mg, 1.283 mmol) in THF (6.0 mL) was added 5 M sodium hydroxide methanolic solution (1.8 mL, 0.009 mmol). After 10 min the solvent was removed under reduced pressure, sat. ammonium chloride solution (5.0 mL) was added and the mixture evaporated to dryness. The resulting solid was triturated with water to afford 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine. 1H NMR (d6-DMSO, 400 MHz) 6.90(1H, s) and 8.55 (1H, s).

Workup

  1. customAfter 10 min the solvent was removed under reduced pressure, sat. ammonium chloride solution (5.0 mL)
  2. additionwas added
  3. customthe mixture evaporated to dryness
  4. customThe resulting solid was triturated with water

Sources & evidence

ORD record
ord-5c4292f5fdf44d3bbda0ba002cbe80b5
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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