Phenacyl bromide → 3-(8-chloro-6-fluoro-3-phenyl-2H-1,4-benzoxazin-5-yl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidindione

HRID 1368019Notes

Reaction equation

HRID 1368019 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].[CH2:24](Br)[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:9][C:6]1[C:7]2[O:8][CH2:24][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N: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 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 120569121-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 120569113-(8-chloro-6-fluoro-3-phenyl-2H-1,4-benzoxazin-5-yl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidindioneYield 18.7%

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)-pyrimidinedione (0.5 g), phenacyl bromide (0.29 g) and potassium carbonate (0.2 g) in acetone (30 ml) was stirred under reflux conditions for 1 hour. Then insoluble salt was removed through Celite and the filtrate concentrated under reduced pressure. The oily substance was purified by column chromatography on silica gel using ethyl acetate-hexane(1:4) as eluent to give the title compound (0.12 g).

Workup

  1. customThen insoluble salt was removed through Celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe oily substance was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4b90007f77b04608a4a49043146466ae
Source dataset
uspto-grants-2003_06
Patent number
US06573218B1

Reaction notes

Loading…