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Sodium hydride → 5-{4-Fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}-4-(methoxycarbonyl)methoxypyrimidine

HRID 1862268
Notes
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Reaction equation

HRID 1862268 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:5]([O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:6][CH:7]=[N:8][CH:9]=1.F[C:17]1[CH:22]=[C:21]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:25]([CH3:34])[C:24]2=[O:35])[C:20]([F:36])=[CH:19][C:18]=1[N+:37]([O-:39])=[O:38].[Cl-].[NH4+]>CN(C)C=O>[F:36][C:20]1[C:21]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:25]([CH3:34])[C:24]2=[O:35])=[CH:22][C:17]([O:3][C:4]2[C:5]([O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:6][CH:7]=[N:8][CH:9]=2)=[C:18]([N+:37]([O-:39])=[O:38])[CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 121155092,5-Difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzeneHCID 18619216HCID 18619216, compound

Product 1

HCID 186192355-{4-Fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}-4-(methoxycarbonyl)methoxypyrimidine
Yield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 42 mg of Sodium hydride and N,N-dimethylformamide, 0.184 g of 5-hydroxy-4-(methoxycarbonyl)methoxypyrimidine was added and stirred at room temperature for 1 hour. Then 0.35 g of 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene 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 0.448 g of 5-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}-4-(methoxycarbonyl)methoxypyrimidine.

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-a503e6603c924edbb3d8ff652fabdaaa
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06537948B1

Reaction notes

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