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

HRID 1686875Notes

Reaction equation

HRID 1686875 reaction equation
[CH:1]1[C:5]2[C:6]([Cl:10])=[N:7][CH:8]=[N:9][C:4]=2[NH:3][CH:2]=1.[I:11]N1C(=O)CCC1=O>C(Cl)Cl>[CH:2]1[NH:3][C:4]2[N:9]=[CH:8][N:7]=[C:6]([Cl:10])[C:5]=2[C:1]=1[I:11]

Participants

4

Reactant 2

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

Product 1

HCID 148092816-Chloro-7-iodo-7-deazapurine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound dA.23 was synthesized according to the procedure described by Ju et al. (2006, which is incorporated herein by reference). To a suspension of 6-chloro-7-deazapurine (1.00 g, 6.51 mmol) in anhydrous CH2Cl2 (55 mL) was added N-iodosuccinimide (1.70 g, 7.56 mmol). The reaction was protected from light while stirring at room temperature for two hours. The reaction was then concentrated down in vacuo. The material was re-crystallized from hot methanol to yield 6-chloro-7-iodo-7-deazapurine dA.23 (0.94 g, 52%).

Workup

  1. customCompound dA.23 was synthesized
  2. concentrationThe reaction was then concentrated down in vacuo
  3. customThe material was re-crystallized from hot methanol

Sources & evidence

ORD record
ord-129717a43df54a0aaf3c7786a08564f0
Source dataset
uspto-grants-2012_04
Patent number
US08148503B2

Reaction notes

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