Sodium hydride → HCID 18619161, compound

HRID 1862346Notes

Reaction equation

HRID 1862346 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[C:12]([OH:13])=[CH:11][N:10]=[CH:9][N:8]=1.[CH3:32][O:33][C:34](=[O:38])[CH:35](Br)[CH3:36].[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:27])([F:28])[F:29])[N:21]([CH3:30])[C:20]2=[O:31])=[CH:14][C:5]=1[O:6][C:7]1[C:12]([O:13][CH:35]([C:34]([O:33][CH3:32])=[O:38])[CH3:36])=[CH:11][N:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 95576Methyl 2-bromopropionateHCID 18619231HCID 18619231, compound

Product 1

HCID 18619161HCID 18619161, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 32 mg of Sodium hydride and N,N-dimethylformamide, 0.35 g of 4-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-5-hydroxypyrimidine was added and stirred at room temperature for 1 hour. Then 0.135 g of methyl2-bromopropionate was added to the mixture, and stirred for 2 hours at room temperature, then for 1 hour at 50° C. 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 0.319 g of 4-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-5-{1-(methoxycarbonyl)ethoxy}pyrimidine [present compound 3-52].

Workup

  1. additionwas added
  2. stirringstirred for 2 hours at room temperature
  3. waitfor 1 hour at 50° C
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated ammonium chloride solution and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2041fd87ef7248a69c364bfae69ce9d1
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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