N-bromobutanimide → 3-Bromo-5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine

HRID 1878528Notes

Reaction equation

HRID 1878528 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[CH:15][CH:16]=[C:4]2[N:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Br:17][C:16]1[CH:15]=[N:14][N:5]2[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:7][C:2]([Cl:1])=[N:3][C:4]=12

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 585310715-Chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 585310033-Bromo-5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidineYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

There was dissolved, in methylene chloride (2 mL), 5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (100 mg, 0.419 mM), then N-bromo-succinimide (78.8 mg, 0.443 mM) was added to the solution and the mixture was stirred at room temperature for one hour. This reaction liquid was diluted with a saturated aqueous sodium bicarbonate solution and then extracted with ethyl acetate. The extracts thus obtained were combined, dried over anhydrous sodium sulfate and the solvent was then distilled off. The resulting residue was purified by the silica gel column chromatography (methylene chloride) to thus give the title compound (80.7 mg, yield: 61%).

Workup

  1. customThis reaction liquid
  2. extractionextracted with ethyl acetate
  3. customThe extracts thus obtained
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled off
  6. customThe resulting residue was purified by the silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-2068f934617a4756a3adfe7cbbc13970
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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