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

HRID 1403255
Notes
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Reaction equation

HRID 1403255 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[I:12]N1C(=O)CCC1=O.O>ClCCl>[I:12][C:11]1[C:4]2[C:3]([O:2][CH3:1])=[N:8][CH:7]=[N:6][C:5]=2[NH:9][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 2487924-Methoxy-7h-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 579631375-iodo-4-methoxy-7H-pyrrolo[2,3-d]pyrimidineYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-methoxy-7H-pyrrolo[2,3-d]pyrimidine (3, 3.20 g, 21.4 mmol) in 280 mL of dichloromethane, N-iodosuccinimide (5.3 g, 24.0 mmol) suspended in dichloromethane was added. The reaction was stirred at room temperature for 2 hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was washed with ethyl acetate and hexane to provide the desired compound (35, 4.80 g).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. washThe resulting material was washed with ethyl acetate and hexane

Sources & evidence

ORD record
ord-67d5b7904f5c4a02863713142b6ba0d1
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08912204B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes