Bromine → HCID 86723528, compound

HRID 2201293Notes

Reaction equation

HRID 2201293 reaction equation
[C:1]([C:9]1[C:10](=[O:21])[N:11]([CH2:19][CH3:20])[C:12](=[O:18])[N:13]([CH2:16][CH3:17])[C:14]=1[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:22]Br>C(Cl)(Cl)Cl>[C:1]([C:9]1[C:10](=[O:21])[N:11]([CH2:19][CH3:20])[C:12](=[O:18])[N:13]([CH2:16][CH3:17])[C:14]=1[CH2:15][Br:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24408Bromine3×HCID 86723526HCID 86723526, compound

Product 1

HCID 86723528HCID 86723528, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

5-Benzoyl-1,3-diethyl-6-methylpyrimidine-2,4(1H,3H)-dione (step 2)(800 mg, 2.79 mmol) was dissolved in chloroform (Volume: 60 mL) and bromine (0.288 mL, 5.59 mmol) was added. The mixture was heated at 60° C. for 1 h. A further portion of bromine (0.288 mL, 5.59 mmol) was added. The mixture was heated for 30 mins and further bromine (0.288 mL, 5.59 mmol) was added. The reaction mixture was cooled to RT and washed with aqueous sodium metabisulfite. The organic phase was separated, passed through a hydrophobic frit and evaporated under vacuum. The residue was dissolved in DCM and evaporated onto silica. The silica was deposited onto a 10 g silica cartridge and the system eluted with 20% EtOAc/hexane, 30% EtOAc/hexane, and 40% EtOAc/hexane.

Workup

  1. temperatureThe mixture was heated for 30 mins
  2. temperatureThe reaction mixture was cooled to RT
  3. washwashed with aqueous sodium metabisulfite
  4. customThe organic phase was separated
  5. customevaporated under vacuum
  6. dissolutionThe residue was dissolved in DCM
  7. customevaporated onto silica
  8. washthe system eluted with 20% EtOAc/hexane, 30% EtOAc/hexane, and 40% EtOAc/hexane

Sources & evidence

ORD record
ord-c3d8a37a759141319289b6404ba07f99
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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