Sodium hydride → HCID 18619258, compound

HRID 1862278Notes

Reaction equation

HRID 1862278 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])=[CH:14][C:5]=1[O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[OH:13].Br[CH2:33][C:34]([O:36][CH3:37])=[O:35].[Cl-].[NH4+]>CN(C)C=O>[Cl:3][C:4]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])=[CH:14][C:5]=1[O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[O:13][CH2:33][C:34]([O:36][CH3:37])=[O:35]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 178480549HCID 178480549, compound

Product 1

HCID 18619258HCID 18619258, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 30 mg of sodium hydride and N,N-dimethylformamide, 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}-4-hydroxypyridine was added and stirred at room temperature for 1 hour. Then 0.114 g of methyl bromoacetate was added to the mixture, and stirred for 8 hours at room temperature. The mixture was poured into saturated ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride solution and saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 27 mg of 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-(methoxycarbonyl)methoxypyridine [present compound 7-42].

Workup

  1. additionwas added
  2. stirringstirred for 8 hours at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated ammonium chloride solution and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31ada9dfc364427689e4fd1fcf3388b5
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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