Acetonitrile → 5-Iodo-7H-pyrrolo[2,3-d]pyrimidine

HRID 1025615Notes

Reaction equation

HRID 1025615 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[CH:4]=[N:3][CH:2]=1.[I:10]N1C(=O)CCC1=O.C(#N)C>O>[I:10][C:9]1[C:5]2[CH:4]=[N:3][CH:2]=[N:1][C:6]=2[NH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 120273N-IodosuccinimideHCID 2615917H-Pyrrolo(2,3-d)pyrimidine

Product 1

HCID 106103365-Iodo-7H-pyrrolo[2,3-d]pyrimidineYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 250 mL round-bottomed flask, 7H-pyrrolo[2,3-d]pyrimidine (4.34 g, 36.4 mmol, Eq: 1.00) and N-iodosuccinimide (8.61 g, 38.3 mmol, Eq: 1.05) were combined with acetonitrile (60 ml) to give a light brown suspension. The reaction mixture was stirred for 3 h. The reaction mixture was poured into 100 mL H2O and extracted with EtOAc (3×50 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was triturated with diethyl ether (2×25 mL) to give 5-iodo-7H-pyrrolo[2,3-d]pyrimidine (7.58 g, 85%) as orange solid.

Workup

  1. customto give a light brown suspension
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was triturated with diethyl ether (2×25 mL)

Sources & evidence

ORD record
ord-28522a2e964f46c6aace1e6df2c35077
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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