HCID 136400717, compound → N-(5-Iodo-7-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide

HRID 598184Notes

Reaction equation

HRID 598184 reaction equation
[I:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[N:6][C:5]=2[N:4]([CH3:19])[C:3]=1I>C(O)(=O)C.O.[Zn]>[I:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([NH:12][C:13](=[O:18])[C:14]([CH3:15])([CH3:17])[CH3:16])=[N:6][C:5]=2[N:4]([CH3:19])[CH:3]=1

Participants

5

Reactant 1

HCID 136400717HCID 136400717, compound

Product 1

HCID 136400716N-(5-Iodo-7-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamideYield 78%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a suspension of N-(5,6-diiodo-7-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide (941 mg, 1.88 mmol) in acetic acid (9 ml) and water (2 ml) was added zinc powder (246 mg, 3.76 mmol), and the mixture was stirred at room temperature for 1 day. After addition of zinc (123 mg, 1.88 mmol), the mixture was stirred at room temperature for 1 day. The reaction mixture was diluted with water and stirred at 0° C. for 2 hours. The resulting crystals were collected by filtration, washed with water and dissolved in tetrahydrofuran. The solution was filtrated, and the filtrate was concentrated in vacuo. The residue was washed with diiopropyl ether to give 545 mg (78%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 day
  2. stirringstirred at 0° C. for 2 hours
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with water
  5. dissolutiondissolved in tetrahydrofuran
  6. filtrationThe solution was filtrated
  7. concentrationthe filtrate was concentrated in vacuo
  8. washThe residue was washed with diiopropyl ether

Sources & evidence

ORD record
ord-cc001a87d7ce4ae3b050054372b96f01
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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