Water → HCID 53725342, compound

HRID 1707566Notes

Reaction equation

HRID 1707566 reaction equation
[F:1][C:2]1[C:14]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[NH:17][C:16]2=[O:26])=[CH:13][C:5]2[N:6]([CH2:10][C:11]#[CH:12])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[CH3:27]I.[H-].[Na+].O>CN(C)C=O>[F:1][C:2]1[C:14]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[N:17]([CH3:27])[C:16]2=[O:26])=[CH:13][C:5]2[N:6]([CH2:10][C:11]#[CH:12])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18961694HCID 18961694, compound

Product 1

HCID 53725342HCID 53725342, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[6-fluoro-3-propargyl-2(3H)benzoxazolon-5-yl]-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione (2.0 g) in dimethylformamide (10 g), methyl iodide (0.5 g) and sodium hydride (0.4 g) were added, and the resultant mixture was heated at 40° to 50° C. for 3 hours. After completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography to give 1-[6-fluoro-3-propargyl-2(3H) -benzoxazolon-5-yl]-3-methyl -4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione (0.3 g ).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5e64d2c66f264066b8be6c5a5670ef1b
Source dataset
uspto-grants-1994_10
Patent number
US05354730

Reaction notes

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