(3-Trifluoromethylphenyl)urea → Allyl(rac)-4-[4-cyano-2-(methylsulfonyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 707566Notes

Reaction equation

HRID 707566 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[S:11]([CH3:14])(=[O:13])=[O:12])=O.[F:15][C:16]([F:28])([F:27])[C:17]1[CH:18]=[C:19]([NH:23][C:24]([NH2:26])=[O:25])[CH:20]=[CH:21][CH:22]=1.[C:29]([O:35][CH2:36][CH:37]=[CH2:38])(=[O:34])[CH2:30][C:31]([CH3:33])=O>CC(OC)(C)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:30]([C:29]([O:35][CH2:36][CH:37]=[CH2:38])=[O:34])=[C:31]([CH3:33])[N:23]([C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:27])([F:28])[F:15])[CH:18]=3)[C:24](=[O:25])[NH:26]2)=[C:4]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:5]=1)#[N:8]

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 70701Allyl acetoacetateHCID 581337504-Formyl-3-(methylsulfonyl)benzonitrile

Product 1

HCID 42642358Allyl(rac)-4-[4-cyano-2-(methylsulfonyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

The mixture was then diluted with MTBE (450 ml), and 4-formyl-3-(methylsulfonyl)benzonitrile (22.00 g, 105 mmol; Example 4A), 1-[3-(trifluoromethyl)phenyl]urea (21.47 g, 105 mmol) and allyl acetoacetate (22.42 g, 158 mmol) were added. The mixture was stirred under reflux overnight. Since the reaction was incomplete, the reaction mixture was concentrated by distillative removal of 350 ml of MTBE. The mixture was then heated under reflux for a further 4 h. For work-up, the solvent was removed under reduced pressure, and the residue was suspended in diethyl ether and then filtered off with suction. The solid was washed with dist. water (350 ml) and then with diethyl ether (50 ml). This gave 34.74 g (64% of theory) of the title compound.

Workup

  1. additionwere added
  2. temperatureunder reflux overnight
  3. concentrationthe reaction mixture was concentrated by distillative removal of 350 ml of MTBE
  4. temperatureThe mixture was then heated
  5. temperatureunder reflux for a further 4 h
  6. customFor work-up, the solvent was removed under reduced pressure
  7. filtrationfiltered off with suction
  8. washThe solid was washed with dist

Sources & evidence

ORD record
ord-2772c3aaf83b410d8dccec8a76c18b82
Source dataset
uspto-grants-2015_11
Patent number
US09174997B2

Reaction notes

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