Dichloromethane → 1-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

HRID 1265350Notes

Reaction equation

HRID 1265350 reaction equation
[NH2:1][C:2]1[C:7]([O:8]C)=[C:6]([Cl:10])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]1=[O:24].C(Cl)Cl>ClCCCl>[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:10])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]1=[O:24]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 183145373-(2-Amino-4-chloro-6fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)pyrimidinedione

Product 1

HCID 120569121-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneYield 62.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-(2-Amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (1.1 g, 2.7 mmol) was dissolved in 50 ml of anhydrous 1,2-dichloroethane and 3.4 g (10.8 mmol) of borontribromide-dimethylsulfide complex was added to the solution. The solution was refluxed for 16 hr and, methylene chloride (100 ml) was added. Washing with water followed by drying (anhydrous sodium sulfate) and removal of the solvent afforded a residue which was triturated with ether to afford the title compound (0.6 g).

Workup

  1. addition3.4 g (10.8 mmol) of borontribromide-dimethylsulfide complex was added to the solution
  2. temperatureThe solution was refluxed for 16 hr
  3. washWashing with water
  4. customby drying
  5. custom(anhydrous sodium sulfate) and removal of the solvent
  6. customafforded a residue which
  7. customwas triturated with ether

Sources & evidence

ORD record
ord-42618e91d4a34d4e85e415a5497284a2
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

Loading…