N-Iodosuccinimide → 7-(1-Propyl-butyl)-3-iodo-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1660734Notes

Reaction equation

HRID 1660734 reaction equation
[CH2:1]([CH:4]([C:8]1[N:13]2[N:14]=[C:15]([CH3:17])[CH:16]=[C:12]2[N:11]=[C:10]([CH3:18])[CH:9]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[I:19]N1C(=O)CCC1=O>C(#N)C.ClCCl>[CH2:1]([CH:4]([C:8]1[N:13]2[N:14]=[C:15]([CH3:17])[C:16]([I:19])=[C:12]2[N:11]=[C:10]([CH3:18])[CH:9]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 248985217-(1-Propyl-butyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 248985247-(1-Propyl-butyl)-3-iodo-2,5-dimethyl-pyrazolo[1,5-a]pyrimidineYield 236.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Dissolve 7-(1-propyl-butyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (3.08 g, 12.5 mmol) in anhydrous acetonitrile (25 mL) and add 6 portions (0.70 g each) of N-iodosuccinimide (4.2 g, 18.7 mmol) at 10 minute intervals. Stir over the weekend at room temperature. Strip off the acetonitrile and dilute the oil with dichloromethane (100 mL). Wash with saturated ammonium chloride solution (2×50 mL). Collect the organic phase, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure to yield a dark red oil. Purify the oil using flash chromatography, eluting with 100% hexane/0% (20% ethyl acetate/hexane) to 0% hexane/100% (20% ethyl acetate/hexane) in a step gradient of 50% increments to give an orange oil (10.97 g, 87%).

Workup

  1. washWash with saturated ammonium chloride solution (2×50 mL)
  2. customCollect the organic phase
  3. dry with materialdry over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto yield a dark red oil
  7. customPurify the oil
  8. washeluting with 100% hexane/0% (20% ethyl acetate/hexane) to 0% hexane/100% (20% ethyl acetate/hexane) in a step gradient of 50% increments

Sources & evidence

ORD record
ord-1afc16b4696e4d448c6abe2051daab18
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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