Dimethylformamide → HCID 67365819, compound

HRID 245772Notes

Reaction equation

HRID 245772 reaction equation
[CH3:1][N:2]1[CH2:6][CH:5]([C:7]2[N:11]3[CH:12]=[CH:13][N:14]=[C:15]([CH3:16])[C:10]3=[CH:9][N:8]=2)[CH2:4][C:3]1=[O:17].CN(C)C=O.[Br:23]N1C(=O)CCC1=O>O>[Br:23][C:9]1[N:8]=[C:7]([CH:5]2[CH2:6][N:2]([CH3:1])[C:3](=[O:17])[CH2:4]2)[N:11]2[CH:12]=[CH:13][N:14]=[C:15]([CH3:16])[C:10]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 67363450HCID 67363450, compound

Product 1

HCID 67365819HCID 67365819, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Methyl-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)pyrrolidin-2-one (293 mg, 1.27 mmol) was dissolved N,N-dimethylformamide (12 ml) and N-bromosuccinimide (227 mg, 1.27 mmol) was added and reation mixture was stirred at room temperature overnight. Then water was added to the reaction mixture and extracted with chloroform/iso-propanol (9/1) three times. The combined organic layers were dried (Na2SO4) and concentrated in vacuo and a brown oil was obtained. The residue was purified by column chromatography (silica gel; dichloromethane/methanol/heptane=9/1/4) to give 4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)-1-methylpyrrolidin-2-one (200 mg).

Workup

  1. additionwas added
  2. extractionextracted with chloroform/iso-propanol (9/1) three times
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customa brown oil was obtained
  6. customThe residue was purified by column chromatography (silica gel; dichloromethane/methanol/heptane=9/1/4)

Sources & evidence

ORD record
ord-83770696072244af8e209d0a276ce822
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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