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

HRID 253707노트

반응식

HRID 253707 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-35149a4e37384af7b86cab7ab268a409
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872129B2

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