Benzoyl Peroxide → HCID 69023349, compound

HRID 217899Notes

Reaction equation

HRID 217899 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[NH:5][CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]2[C:13](=[O:23])[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][N:18]=3)[N:16]=[C:7]12)[CH3:2].[Br:25]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:24])[NH:5][CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]2[C:13](=[O:23])[C:14]([Br:25])=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][N:18]=3)[N:16]=[C:7]12)[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 69026638HCID 69026638, compound

Product 1

HCID 69023349HCID 69023349, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 0.080 g (0.24 mmol) of (4-oxo-2-pyrimidin-4-yl -4,6,7,8,9,10-hexahydro-pyrimido[1,2-a]azepin-10-yl)-carbamic acid ethyl ester in dimethylformamide (4 mL) were added 0.21 g (1.21 mmol) of N-bromosuccinimide and 0.03 g (0.12 mmol) of benzoyl peroxide. The solution was stirred at room temperature for 10 min and at 50° C. for 20 min. The reaction was quenched by adding a saturated solution of ammonium chloride. The product was extracted with dichloromethane, the organic phase was washed with a saturated solution of sodium chloride, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was chromatographed on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 95/5 to afford 58 mg of a solid.

Workup

  1. customThe reaction was quenched
  2. additionby adding a saturated solution of ammonium chloride
  3. extractionThe product was extracted with dichloromethane
  4. washthe organic phase was washed with a saturated solution of sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was chromatographed on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 95/5

Sources & evidence

ORD record
ord-8b9ae9c1b674455098d2a6e2ea635048
Source dataset
uspto-grants-2012_06
Patent number
US08198287B2

Reaction notes

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