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

HRID 277401

Reaction equation

HRID 277401 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-6trifluoromethyl-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 imethylsulfide 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 imethylsulfide 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-5a7f1aac39f3483da73a2db568028b8f
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Linked notes

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