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

HRID 707583Notes

Reaction equation

HRID 707583 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[S:11][CH3:12])=O.[F:13][C:14]([F:26])([F:25])[C:15]1[CH:16]=[C:17]([NH:21][C:22]([NH2:24])=[O:23])[CH:18]=[CH:19][CH:20]=1.[C:27]([O:33][CH2:34][CH:35]=[CH2:36])(=[O:32])[CH2:28][C:29]([CH3:31])=O>CC(OC)(C)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:28]([C:27]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])=[C:29]([CH3:31])[N:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:25])([F:26])[F:13])[CH:16]=3)[C:22](=[O:23])[NH:24]2)=[C:4]([S:11][CH3:12])[CH:5]=1)#[N:8]

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 70701Allyl acetoacetateHCID 581337424-Formyl-3-(methylsulfanyl)benzonitrile

Product 1

HCID 44133410Allyl(rac)-4-[4-cyano-2-(methylsulfanyl)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 (27 ml), and 4-formyl-3-(methylsulfanyl)benzonitrile (1.18 g, 6.70 mmol; Example 9A), 1-[3-(trifluoromethyl)phenyl]urea (1.37 g, 6.70 mmol) and allyl acetoacetate (1.43 g, 10.1 mmol) were added. The mixture was stirred under reflux overnight. For work-up, the solvent was removed under reduced pressure and the residue was suspended in diethyl ether and then filtered of with suction. This gave 978 mg (19% of theory) of the title compound.

Workup

  1. additionwere added
  2. temperatureunder reflux overnight
  3. customFor work-up, the solvent was removed under reduced pressure
  4. filtrationfiltered of with suction

Sources & evidence

ORD record
ord-add067b584e94eaea548864e07c1cd16
Source dataset
uspto-grants-2015_11
Patent number
US09174997B2

Reaction notes

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