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

HRID 1725593ノート

反応式

HRID 1725593 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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). 1H-NMR (500 MHz, DMSO-d6) δ 12.7 (br s, 1H), 7.87 (d, J=7.6 Hz, 1H), 7.79 (m, 2H), 7.73 (d, J=7.5 Hz, 1H), 6.32 (s, 1H), 1.93 (m, 1H), 0.90 (m, 4H), [urea: 10.8 (br s, 1H), 7.45 (br s, 1H)] ppm; LC-MS 280.96 (M+H); Rt (Method A) 2.961 minutes (title compound), 2.313 minutes (urea impurity).

後処理

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

出典と根拠

ORDレコード
ord-d56bc59d835d4ea9974163eba88df52e
出典データセット
uspto-grants-2009_02
特許番号
US07491730B2

反応ノート

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