Urea → 4-(3,5-Bis-trifluoromethylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid amide

HRID 2183553Notes

Reaction equation

HRID 2183553 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[C:17]([NH2:23])(=[O:22])[CH2:18][C:19]([CH3:21])=O.[NH2:24][C:25]([NH2:27])=[O:26].B(F)(F)F.CCOCC>[Cu](Cl)Cl.C1COCC1.CC(O)=O>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:6]2[C:18]([C:17]([NH2:23])=[O:22])=[C:19]([CH3:21])[NH:27][C:25](=[O:26])[NH:24]2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1

Participants

8

Reactant 4

HCID 1176UreaHCID 8000Boron trifluoride etherateHCID 80077AcetoacetamideHCID 1362473,5-Bis(trifluoromethyl)benzaldehyde

Product 1

HCID 865860054-(3,5-Bis-trifluoromethylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid amideYield 36.2%

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3,5-bis(trifluoromethyl)benzaldehyde (2.42 g, 10.0 mmol), acetoacetamide (1.01 g, 10.0 mmol), urea (0.90 g, 15.0 mmol), copper chloride (0.1 g, 1.0 mmol), boron trifluoride etherate (0.09 mL), AcOH (0.04 mL), and THF (20 mL) was heated at 65° C. for 18 h and cooled to room temperature. The resulting precipitates were collected by vacuum filtration, washed with THF, and air dried to give the title compound as an off-white solid (1.33 g, 36%).

Workup

  1. temperaturecooled to room temperature
  2. customThe resulting precipitates
  3. filtrationwere collected by vacuum filtration
  4. washwashed with THF, and air
  5. customdried

Sources & evidence

ORD record
ord-56dcc4c1e5f845048640199c8dff261c
Source dataset
uspto-grants-2005_05
Patent number
US06900214B2

Reaction notes

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