Water → 4-ethoxy-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

HRID 1396136Notes

Reaction equation

HRID 1396136 reaction equation
[CH2:1]([O:3][C:4]1[C:5]2[CH:12]=[CH:11][NH:10][C:6]=2[N:7]=[CH:8][N:9]=1)[CH3:2].CN(C)C=O.[I:18]N1C(=O)CCC1=O.O>ClCCl>[CH2:1]([O:3][C:4]1[C:5]2[C:12]([I:18])=[CH:11][NH:10][C:6]=2[N:7]=[CH:8][N:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 579632454-ethoxy-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 584858444-ethoxy-5-iodo-7H-pyrrolo[2,3-d]pyrimidineYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-ethoxy-7H-pyrrolo[2,3-d]pyrimidine (11, 1.60 g, 9.8 mmol) in 50.0 mL of dichloromethane, N,N-dimethylformamide (2.0 mL, 26 mmol) and N-iodosuccinimide (2.40 g, 10.7 mmol) are added and the reaction stirred at room temperature for 2 hours. The reaction is poured into water and extracted with ethyl acetate. The organic layer is dried with sodium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound (12, 2.70 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-61521db4c0584885bcec8006230888f5
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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