Dichloromethane → 4-{[2-Chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine

HRID 38768

反応式

HRID 38768 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12](Cl)=[O:13])=[CH:4][N:3]=1.ClCCl.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(N(CC)CC)C>O.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:13])=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 8471TriethylamineHCID 27367082-Chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl chloride

生成物 1

HCID 581687074-{[2-Chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-70 °C

実験手順

A mixture of 2-chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl chloride (2.8 g) and dichloromethane (56 mL) was cooled in a dry ice-acetone bath, and morpholine (990 μL) and triethylamine (1.9 mL) were added dropwise thereto while keeping the temperature at −50° C. or lower. The reaction mixture was stirred at −70° C. for 2.5 hours, and then ethyl acetate and water were added thereto. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain 4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine (2.8 g) as a white solid.

後処理

  1. temperaturewas cooled in a dry ice-acetone bath
  2. customat −50° C.
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-67953608ec5b4129a0de88b6f59f7c5b
出典データセット
uspto-grants-2013_09
特許番号
US08524727B2

関連ノート

読み込み中…