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

HRID 509930Notes

Reaction equation

HRID 509930 reaction equation
[CH3:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[I:11]N1C(=O)CCC1=O>ClCCl>[I:11][C:10]1[C:3]2[C:2]([CH3:1])=[N:7][CH:6]=[N:5][C:4]=2[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 513419594-Methyl-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 582592995-iodo-4-methyl-7H-pyrrolo[2,3-d]pyrimidineYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-methyl-7H-pyrrolo[2,3-d]pyrimidine (18, 0.634 g, 4.76 mmol) in 50 mL of dichloromethane, N-iodosuccinimide (1.3 g, 5.7 mmol) was added and the reaction stirred at room temperature for 45 minutes. The reaction was concentrated under vacuum, then ethyl acetate was added and washed with 1 N aqueous sodium thiosulfate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (19, 0.94 g). MS (ESI) [M+H+]+=260.26.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. additionethyl acetate was added
  3. washwashed with 1 N aqueous sodium thiosulfate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material was purified by silica gel column chromatography
  8. washeluting with 20-100% ethyl acetate in hexane
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-96a101577cbc4cb9bc9cede27d7906fd
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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