Sodium hydride → HCID 19103940, compound

HRID 1198099Notes

Reaction equation

HRID 1198099 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][F:11])=[CH:6][C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[NH:14][C:13]2=[O:23])=[C:4]([F:24])[CH:3]=1.[H-].[Na+].[N+:27](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>CN(C)C=O>[NH2:27][N:14]1[C:15]([C:19]([F:21])([F:22])[F:20])=[CH:16][C:17](=[O:18])[N:12]([C:5]2[CH:6]=[C:7]([O:8][CH2:9][CH2:10][F:11])[C:2]([Br:1])=[CH:3][C:4]=2[F:24])[C:13]1=[O:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 19103944HCID 19103944, compound

Product 1

HCID 19103940HCID 19103940, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-[4-bromo-2-fluoro-5-(2-fluoroethoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (0.4 g) in N,N-dimethylformamide (10 ml) are added dropwise to a suspension of 60% sodium hydride (0.05 g) in N,N-dimethylformamide (10 ml) at 5° to 10° C. The mixture is allowed to stir at 10° to 20° C. for additional 30 minutes. To the mixture, 2,4-dinitrophenoxyamine (0.22 g) is added slowly at 10° to 20° C., followed by stirring at room temperature for one hour. The reaction mixture is poured into ice water and extracted with ethyl acetate. The extract is washed with water, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel chromatography to give 1-amino-3-[4-bromo-2-fluoro-5-(2-fluoroethoxy)phenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione.

Workup

  1. stirringby stirring at room temperature for one hour
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-832572141207426aaf042109d8bd6a98
Source dataset
uspto-grants-1994_01
Patent number
US05280010

Reaction notes

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