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

HRID 38768

반응식

HRID 38768 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-67953608ec5b4129a0de88b6f59f7c5b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524727B2

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