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

HRID 333480Notes

Reaction equation

HRID 333480 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-b749bf6e24074e40aa4bebb2d3b49429
Source dataset
uspto-grants-2014_11
Patent number
US08877905B2

Reaction notes

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