N-Iodosuccinimide → 6-Chloro-7-iodo-7-deazapurine

HRID 1187283Notes

Reaction equation

HRID 1187283 reaction equation
[Cl: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>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 148092816-Chloro-7-iodo-7-deazapurineYield 62.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 1.21 g, 7.88 mmol) dissolved in 50 mL of dichloromethane, N-iodosuccinimide (1.95 g, 8.67 mmol) is added and the reaction is stirred at room temperature overnight. The reaction is quenched with 50% aqueous sodium thiosulfate and the mixture is filtered through celite. The aqueous layer is extracted with ethyl acetate. The organic layers are combined and washed with water, then brine, and dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (27, 1.383 g). MS (ESI) [M+H+]+=279.8, 281.8.

Workup

  1. customThe reaction is quenched with 50% aqueous sodium thiosulfate
  2. filtrationthe mixture is filtered through celite
  3. extractionThe aqueous layer is extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialbrine, and dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material is purified by silica gel column chromatography
  9. washeluting with ethyl acetate and dichloromethane
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6aa892e8a0c84d85bc76d1d32c069fcd
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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