Benzoyl Peroxide → HCID 21112413, compound

HRID 2373509Notes

Reaction equation

HRID 2373509 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:9]([O:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:8]=[C:7]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:6]=1)=[O:4].[Br:36]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:10]([O:11][C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:9]([O:20][C:21](=[O:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:8]=[C:7]([CH:29]([Br:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 16221115HCID 16221115, compound

Product 1

HCID 21112413HCID 21112413, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl-5,6-bis(benzoyloxy)-2-benzylpyrimidine-4-carboxylate (B-6) (1.0 eq.) in carbon tetrachloride was heated up to 90° C. under nitrogen; N-bromosuccinimide (1.0 eq.) and benzoyl peroxide (0.1 eq.) were added as dry powder and mixture was refluxed for 3 h. After cooling, succinimide was removed by filtration and the filtrate was concentrated and purified by flash column chromatography (SiO2, 85/15 v/v petroleum ether/ethyl acetate as eluent) to give the title product (B-7).

Workup

  1. customas dry powder and mixture
  2. temperaturewas refluxed for 3 h
  3. temperatureAfter cooling
  4. customsuccinimide was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. custompurified by flash column chromatography (SiO2, 85/15 v/v petroleum ether/ethyl acetate as eluent)

Sources & evidence

ORD record
ord-042e6c2901c44e34b85eb51c36ca7f51
Source dataset
uspto-grants-2008_12
Patent number
US07459452B2

Reaction notes

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