Acetic Acid → 6-cyclopropyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-one

HRID 253707Notes

Reaction equation

HRID 253707 reaction equation
[CH:1]1([C:4]([N:6](C)C)=[CH2:5])[CH2:3][CH2:2]1.[F:9][C:10]([F:23])([F:22])[C:11]1[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=1[C:13]([N:15]=[C:16]=[O:17])=O.C([O-])(=O)C.[NH4+].C(O)(=O)C>O1CCCC1.O>[CH:1]1([C:4]2[N:6]=[C:13]([C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[C:10]([F:23])([F:22])[F:9])[NH:15][C:16](=[O:17])[CH:5]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 17979386(1-Cyclopropylvinyl)dimethylamineHCID 21202676Benzoyl isocyanate, 2-(trifluoromethyl)-

Product 1

HCID 1355815616-cyclopropyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-oneYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of (1-cyclopropyl-vinyl)-dimethylamine in tetrahydrofuran (400 mL) at 0° C. under nitrogen was added a solution of 2-trifluoromethylbenzoyl isocyanate in tetrahydrofuran (50 mL), in a dropwise fashion. The reaction was stirred for 0.5 hour, then ammonium acetate (78 g, 1000 mmol) and acetic acid (400 mL) was added. The reaction mixture was heated at reflux for 3 hours with continuous removal of tetrahydrofuran, then cooled and poured into water (1.2 L). The resulting precipitate was collected by filtration, washing with water and ether to provide 6-cyclopropyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-one (28.79 g, 56% yield) as a white solid which is a mixture of the title compound and (2-trifluoromethyl-benzoyl)-urea (91:9 by HPLC).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashing with water and ether

Sources & evidence

ORD record
ord-35149a4e37384af7b86cab7ab268a409
Source dataset
uspto-grants-2011_01
Patent number
US07872129B2

Reaction notes

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