Hydrogen Bromide → HCID 18619167, compound

HRID 1862309Notes

Reaction equation

HRID 1862309 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11]CC(OC)=O)=[N:9][CH:10]=1.Br.C(=O)(O)[O-].[Na+]>>[Cl:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8](=[O:11])[NH:9][CH:10]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 18619155HCID 18619155, compound2×

Product 1

HCID 18619167HCID 18619167, compoundYield 87.5%

Procedure

A mixture of 0.08 g of 5-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxypyridine [present compound 7-17] and 1 ml of 48% hydrobromic acid was stirred at reflux temperature for 3 hours. The mixture was neutralized with saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated to obtain 0.06 g of 5-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-pyridone.

Workup

  1. temperatureat reflux temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ea191e9a57794404b6a80407d52f7382
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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