N-methyl-2-pyrrolidone → HCID 18759293, compound

HRID 433734Notes

Reaction equation

HRID 433734 reaction equation
[F:1][C:2]1[C:3]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]2=[O:30])=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[C:6](Br)[CH:7]=1.[Cu](C#N)[C:32]#[N:33].CN1CCCC1=O>O>[F:1][C:2]1[C:3]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]2=[O:30])=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[C:6]([C:32]#[N:33])[CH:7]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 18759297HCID 18759297, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 18759293HCID 18759293, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 75 mg of 5-fluoro-2-(3-methoxyphenoxy)-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]bromobenzene, 27 mg of copper cyanide and 0.5 ml of N-methyl-2-pyrrolidone was stirred at 170 to 180° C. for 2 hours. The reaction mixture was cooled to room temperature, water was added to the mixture and the resultant was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 57 mg of 5-fluoro-2-(3-methoxyphenoxy)-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]cyanobenzene.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe resultant was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e95c1629de24221bc71d78a825e522e
Source dataset
uspto-grants-2003_12
Patent number
US06667413B2

Reaction notes

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