Water → HCID 58981004, compound

HRID 1181843Notes

Reaction equation

HRID 1181843 reaction equation
[CH:1]1([CH2:4][N:5]2[C:10]3=[N:11][NH:12][CH:13]=[C:9]3[C:8](=[O:14])[N:7]([CH3:15])[C:6]2=[O:16])[CH2:3][CH2:2]1.[Br:17]N1C(=O)CCC1=O.O>ClCCCl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:17][C:13]1[NH:12][N:11]=[C:10]2[C:9]=1[C:8](=[O:14])[N:7]([CH3:15])[C:6](=[O:16])[N:5]2[CH2:4][CH:1]1[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 178481351HCID 178481351, compound

Product 1

HCID 58981004HCID 58981004, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 111,2-DichloroethaneSolvent

Procedure

7-(Cyclopropylmethyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (6.0 g), N-bromosuccinimide (7.8 g), and 100 mg of AIBN was taken up in 50 mL of 1,2-dichloroethane. The heterogeneous mixture was brought to reflux overnight. Water (100 mL) was added to the solution and separated. The organic layer was dried over sodium sulfate, filtered and removed under reduced pressure to give a yellow solid. The compound was flashed through a plug of silica gel, gave 6.7 g of white powder.

Workup

  1. temperatureto reflux overnight
  2. customseparated
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customremoved under reduced pressure
  6. customto give a yellow solid

Sources & evidence

ORD record
ord-6e64da994f8f4f28b406285fb2c0d085
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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