N-Iodosuccinimide → 2-pivaloyl-4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

HRID 1614171Notes

Reaction equation

HRID 1614171 reaction equation
[Al].[C:2]([C:8]1[N:9]=[C:10]([Cl:17])[C:11]2[CH:16]=[CH:15][NH:14][C:12]=2[N:13]=1)(=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[I:18]N1C(=O)CCC1=O>C1COCC1>[C:2]([C:8]1[N:9]=[C:10]([Cl:17])[C:11]2[C:16]([I:18])=[CH:15][NH:14][C:12]=2[N:13]=1)(=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 5359268AluminumHCID 197731592-pivaloyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 197731582-pivaloyl-4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidineYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 ml round bottom flask covered with aluminum foil was charged 1.50 g (5.94 mmol) of 2-pivaloyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidine dissolved in 30 ml of anhydrous THF, followed by the addition of 1.47 g (6.5 mmol) of N-iodosuccinimide. The dark brown solution was stirred at RT under a nitrogen atmosphere for 1 h. The solvent was removed in vacuo, and the residue was dissolved in CHCl3, washed with water, dried over Na2SO4, and removed in vacuo. The crude residue was then flash chromatographed on silica gel eluting with a gradient of 100% CHCl3 to 2% MeOH/CHCl3. After collecting the correct fractions, the solvents were removed in vacuo to give 1.86 g (83%) of 2-pivaloyl-4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine as a

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in CHCl3
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customremoved in vacuo
  6. customflash chromatographed on silica gel eluting with a gradient of 100% CHCl3 to 2% MeOH/CHCl3
  7. customAfter collecting the correct fractions
  8. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-d7004ae081a34f4b94c04a400594f771
Source dataset
uspto-grants-1993_03
Patent number
US05196424

Reaction notes

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