1,2-Dibromoethane → HCID 18519623, compound

HRID 1368023Notes

Reaction equation

HRID 1368023 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]1=[O:23].Br[CH2:25][CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:9][C:6]1[C:7]2[O:8][CH2:26][CH2:25][NH:1][C:2]=2[C:3]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[C:4]([F:10])[CH:5]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 120569121-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 18519623HCID 18519623, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-primidinedione (0.4 g), 1,2-dibromoethane (0.26 g) and potassium carbonate (0.312 g) in acetone (30 ml) was heated at reflux for 6 hours. The insoluble precipitate was removed through Celite and the filtrate was concentrated to an oil. The oily substance was purified by column chromatography on silica gel using ethyl acetate-hexane (1:2) as eluent to give the title compounds (0.028 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customThe insoluble precipitate was removed through Celite
  4. concentrationthe filtrate was concentrated to an oil
  5. customThe oily substance was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0c0cb557b6bf438cab87d722c1c1d921
Source dataset
uspto-grants-2003_06
Patent number
US06573218B1

Reaction notes

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