Benzoyl Peroxide → HCID 68290339, compound

HRID 538239Notes

Reaction equation

HRID 538239 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][CH2:10][C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:15](=[O:26])[N:14]2[CH:27]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClCCCl>[Br:1][C:27]1[N:14]2[C:15](=[O:26])[N:16]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[CH2:10][Cl:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 682908442-chloromethyl-6-(4-fluoro-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-one

Product 1

HCID 68290339HCID 68290339, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-bromosuccinimide (80.4 mg, 0.45 mmol) was added to a stirred solution of 2-chloromethyl-6-(4-fluoro-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-one (0.114 g, 0.41 mmol) and benzoyl peroxide (9.94 mg, 0.041 mmol) in DCE (3 mL). The mixture was stirred at RT for 16 hours. The solvent was evaporated in vacuo and the crude product was purified by flash column chromatography (silica; AcOEt in DCM with a gradient of 0/100 to 20/80). The desired fractions were collected and the solvents evaporated in vacuo to yield 3-bromo-2-chloromethyl-6-(4-fluoro-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-one (0.102 g, 70% yield) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude product was purified by flash column chromatography (silica
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-25e5f36d14744773a40d474758740326
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

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