Water → HCID 178478352, compound

HRID 1014557Notes

Reaction equation

HRID 1014557 reaction equation
[Cl:1][C:2]1[NH:7][C:6]2=[N:8][CH:9]=[CH:10][C:5]2=[C:4]([Cl:11])[N:3]=1.[I:12]N1C(=O)CCC1=O.O>CN(C=O)C>[Cl:1][C:2]1[NH:7][C:6]2=[N:8][CH:9]=[C:10]([I:12])[C:5]2=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 178418895HCID 178418895, compound

Product 1

HCID 178478352HCID 178478352, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-dichloro-1H-pyrrolo[2,3-d]pyrimidine (0.5 g, 2.66 mmol) was dissolved in anhydrous DMF (20 mL) and N-iodo succinimide (718 mg, 3.19 mmol) was added. After stirring for 45 minutes at rt, reaction mixture was poured into water (400 mL) and extracted with EtOAc (2×500 mL) Organics were combined and washed with brine (500 mL) and dried over sodium sulfate. Solvents were removed under reduced pressure and purified via column chromatography to afford 2,4-dichloro-5-iodo-1H-pyrrolo[2,3-d]pyrimidine (660 mg, 2.103 mmol) as a yellow solid. ESIMS (M+H)+=315

Workup

  1. customreaction mixture
  2. extractionextracted with EtOAc (2×500 mL)
  3. washwashed with brine (500 mL)
  4. dry with materialdried over sodium sulfate
  5. customSolvents were removed under reduced pressure
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-dbb50421baad4654beb97cb939e5b7f4
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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