Methanol → 2-(3-chlorophenyl)-6-(trifluoromethyl)pyrimidin-4(3H)-one

HRID 1508907ノート

反応式

HRID 1508907 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](=[NH:7])[NH2:6].[F:11][C:12]([F:22])([F:21])[C:13](=O)[CH2:14][C:15](OCC)=[O:16].C[O-].[Na+].CO>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:6][C:15](=[O:16])[CH:14]=[C:13]([C:12]([F:22])([F:21])[F:11])[N:7]=2)[CH:8]=[CH:9][CH:10]=1

参加物

6

反応物 4

HCID 887MethanolHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 2041443-Chloro-benzamidineHCID 10942334Sodium Methoxide

生成物 1

HCID 1362248182-(3-chlorophenyl)-6-(trifluoromethyl)pyrimidin-4(3H)-one収率 51.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

A 500-mL round bottomed flask was charged with 3-chlorobenzimidamide (4.81 g, 25.3 mmol), ethyl 4,4,4-trifluoro-3-oxobutanoate (5.00 g, 27.1 mmol), and ethanol (90 mL) and cooled to 0° C. A 25% sodium methoxide solution in methanol (13.0 mL, 55.3 mmol) was added to the mixture. The resulting mixture was stirred at reflux for 20 h. After this time, the mixture was cooled to room temperature and concentrated under reduced pressure to 25 mL. The residual slurry was cautiously treated with 2N HCl (50 mL) forming a solid. The solid was collected by filtration and washed with water followed by ether to afford the title compound (3.60 g, 48%) as a white solid, which was carried forward into the next step without further purification. MW=274.63. 1H NMR (DMSO-d6, 500 MHz) δ 13.39 (s, 1H), 8.18 (s, 1H), 8.10 (d, J=7.5 Hz, 1H), 7.73-7.69 (m, 1H), 7.60 (t, J=8.0 Hz, 1H), 6.94 (s, 1H).

後処理

  1. temperatureat reflux for 20 h
  2. temperatureAfter this time, the mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure to 25 mL
  4. additionThe residual slurry was cautiously treated with 2N HCl (50 mL)
  5. customforming a solid
  6. filtrationThe solid was collected by filtration
  7. washwashed with water

出典と根拠

ORDレコード
ord-8d6573d9cedf45149ba4e3cd1e79c8a7
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

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