N-Iodosuccinimide → 4-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

HRID 1692836Notes

Reaction equation

HRID 1692836 reaction equation
[CH:1]1([C:6]2[C:7]3[CH:14]=[CH:13][NH:12][C:8]=3[N:9]=[CH:10][N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[I:15]N1C(=O)CCC1=O>ClCCl>[CH:1]1([C:6]2[C:7]3[C:14]([I:15])=[CH:13][NH:12][C:8]=3[N:9]=[CH:10][N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 116369524-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 579632054-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidineYield 371.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine (48, 0.099 g, 0.53 mmol) was dissolved in 3.4 mL of dichloromethane under an atmosphere of nitrogen and N-iodosuccinimide (0.131 g, 0.582 mmol) was added. The mixture was stirred overnight, then quenched with aqueous sodium thiosulfate. The aqueous layer was separated and washed with ethyl acetate. The organic layers were combined and washed with water, brine, dried over sodium sulfate and filtered. The filtrate was concentrated under vacuum to provide the desired compound (49, 0.616 g), used in the next step without further purification. MS (ESI) [M+H+]+=313.9.

Workup

  1. customquenched with aqueous sodium thiosulfate
  2. customThe aqueous layer was separated
  3. washwashed with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-42307225dbbc406aafeeabe8ed3d0a3e
Source dataset
uspto-grants-2012_04
Patent number
US08158636B2

Reaction notes

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