Benzoyl Peroxide → 3-bromo-6-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one

HRID 538252Notes

Reaction equation

HRID 538252 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:19]N1C(=O)CCC1=O.[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][C:37]3=[N:40][C:41]([CH2:43][O:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[CH:42][N:36]3[C:35]2=[O:51])=[CH:30][CH:29]=1>ClCCCl>[Br:19][C:42]1[N:36]2[C:35](=[O:51])[N:34]([C:31]3[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=3)[CH2:39][CH2:38][C:37]2=[N:40][C:41]=1[CH2:43][O:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 682902896-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one

Product 1

HCID 682906373-bromo-6-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-oneYield 45.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Benzoyl peroxide (7.2 mg, 0.03 mmol) was added to a stirred solution of N-bromosuccinimide (30.58 mg, 0.33 mmol) and 6-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one (0.1 g, 0.3 mmol) in DCE (5 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 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 3-bromo-6-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one (57 mg, 35% 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-bec4f4a69a644325be01b182dca1ba4f
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

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