Bromine → HCID 58266282, compound

HRID 2039693Notes

Reaction equation

HRID 2039693 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=3)[C:11](=[O:32])[NH:10]2)=[CH:5][CH:4]=1)#[N:2].[Br:33]Br>C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH2:20][Br:33])[N:12]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:29])([F:31])[F:30])[CH:22]=3)[C:11](=[O:32])[NH:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 58266260HCID 58266260, compound

Product 1

HCID 58266282HCID 58266282, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl 4-(4-cyanophenyl)-1-[4-fluoro-3-(trifluoromethyl)phenyl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (447 mg, 1.0 mmol) was dissolved in chloroform (10 ml) and bromine (176 mg, 1.10 mmol) was added at 0° C. The ice bath was removed and the mixture was stirred at room temperature for 0.5 h. The reaction mixture was then diluted with chloroform (20 ml) and washed successively with 10% strength aqueous sodium thiosulphate solution (10 ml) and concentrated aqueous sodium chloride solution (10 ml). The organic phase was separated off, dried over sodium sulphate, filtered and concentrated on a rotary evaporator. This gave 570 mg (quant.) of the target compound which was reacted further without further purification.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction mixture was then diluted with chloroform (20 ml)
  3. washwashed successively with 10% strength aqueous sodium thiosulphate solution (10 ml) and concentrated aqueous sodium chloride solution (10 ml)
  4. customThe organic phase was separated off
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customThis gave 570 mg (quant.) of the target compound which was reacted further without further purification

Sources & evidence

ORD record
ord-c20e6a1bf9d940f09853120f7209e44f
Source dataset
uspto-grants-2013_11
Patent number
US08580800B2

Reaction notes

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