Boron tribromide → 3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-1H-pyridin-2-one

HRID 1354565Notes

Reaction equation

HRID 1354565 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]2=[O:30])=[CH:13][C:3]=1[O:4][C:5]1[C:6]([O:11]C)=[N:7][CH:8]=[CH:9][CH:10]=1.B(Br)(Br)Br>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]2=[O:30])=[CH:13][C:3]=1[O:4][C:5]1[C:6](=[O:11])[NH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22938318HCID 22938318, compound

Product 1

HCID 116549103-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-1H-pyridin-2-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 0.5 g of 3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-2-methoxypyridine and 10 ml of chloroform, 0.5 g of boron tribromide was added and stirred at room temperature for 3 hours. Then the reaction mixture was concentrated. The residue was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and conventrated. The residue was subjected to silica gel column chromatography (eluent: ethyl acetate) to give 0.31 g of 3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-1H-pyridin-2-one.

Workup

  1. additionwas added
  2. concentrationThen the reaction mixture was concentrated
  3. additionThe residue was poured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-e6d057c28240486797bd512e5dbfcd52
Source dataset
uspto-grants-2007_05
Patent number
US07223862B2

Reaction notes

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