Water → 8-(1-Ethylpropyl)-3-iodo-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine

HRID 584788Notes

Reaction equation

HRID 584788 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([CH:11]([N:14]1[C:22]2[N:21]3[N:23]=[C:24]([CH3:26])[CH:25]=[C:20]3[N:19]=[C:18]([CH3:27])[C:17]=2[CH2:16][CH2:15]1)[CH2:12][CH3:13])[CH3:10].O>CN(C)C=O.C(OCC)(=O)C>[CH2:9]([CH:11]([N:14]1[C:22]2[N:21]3[N:23]=[C:24]([CH3:26])[C:25]([I:1])=[C:20]3[N:19]=[C:18]([CH3:27])[C:17]=2[CH2:16][CH2:15]1)[CH2:12][CH3:13])[CH3:10]

Participants

6

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 222495958-(1-ethylpropyl)-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine

Product 1

HCID 222497608-(1-Ethylpropyl)-3-iodo-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidineYield 75.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Iodosuccinimide (3.5 g, 15 mmol) was added to a solution of 8-(1-ethylpropyl)-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (3.7 g 15 mmol) in N,N-dimethylformamide (40 mL) at room temperature, followed by stirring for one hour. Hypo water was added, and the mixture was diluted with ethyl acetate, washed with an aqueous saturated solution of ammonium chloride and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatgraphy (20-40% ethyl acetate/hexane), to give the title compound (4.37 g) as white crystals.

Workup

  1. washwashed with an aqueous saturated solution of ammonium chloride and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel column chromatgraphy (20-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2d542b62983042d3931e4b4c202401b5
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

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