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

HRID 965996Notes

Reaction equation

HRID 965996 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-278ef1d4c3724bc6bfa66545ff97a239
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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