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

HRID 82253

Reaction equation

HRID 82253 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>C(Cl)Cl>[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 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (70.5 g, 0.45 mol) in DCM (1.8 L) was added N-iodosuccinimide (120 g, 0.54 mol) in portions. After addition, the mixture was stirred at room temperature overnight. The solid was filtered and washed with water (250 mL), MeOH (280 mL) and CH2Cl2 (280 mL) sequentially. The solid was dried under vacuum to afford 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine as a brown solid in 79% yield, 107 g.

Workup

  1. additionAfter addition
  2. filtrationThe solid was filtered
  3. washwashed with water (250 mL), MeOH (280 mL) and CH2Cl2 (280 mL) sequentially
  4. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-2c94fdeb27714705b957ca8d9de3bb7e
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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