Triethylamine → 2,4-Dioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile

HRID 576748Notes

Reaction equation

HRID 576748 reaction equation
[C:1]([C:3](=[CH:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[C:4]([NH:6][C:7](=O)[O-:8])=[O:5])#[N:2].C(N(CC)CC)C>C(#N)C>[O:8]=[C:7]1[NH:6][C:4](=[O:5])[C:3]([C:1]#[N:2])=[CH:10][N:11]1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 178511116HCID 178511116, compound

Product 1

HCID 27367422,4-Dioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrileYield 91.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-cyano-3-(3-(trifluoromethyl)phenylamino)acryloylcarbamate (prepared in Reference Example 111) (26.2 g) in acetonitrile (300 ml) was added triethylamine (111 ml) and the resulting mixture was stirred for six hours with heating under reflux. The reaction solutions were concentrated under reduced pressure, and to the residue was added 1M hydrochloric acid and the resulting mixture was extracted with ethyl acetate twice. The organic layer was washed with 1M hydrochloric acid and saturated saline. The resulting mixture was dried over anhydrous magnesium and then concentrated under reduced pressure to afford 2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-carbonitrile (22.7 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. concentrationThe reaction solutions were concentrated under reduced pressure
  4. additionto the residue was added 1M hydrochloric acid
  5. extractionthe resulting mixture was extracted with ethyl acetate twice
  6. washThe organic layer was washed with 1M hydrochloric acid and saturated saline
  7. dry with materialThe resulting mixture was dried over anhydrous magnesium
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e678eb56c199419681a06008cdcfce55
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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