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Water → Morpholine-4-carboxylic Acid 4-trifluoromethyl-pyrimidin-2-yl Ester

HRID 1179870
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HRID 1179870 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([OH:9])[N:4]=1.[N:12]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.N12CCN(CC1)CC2.O>CN(C)C=O.[Cl-].[Na+].O>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][C:18]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:19])[N:4]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 9237DabcoHCID 848104-Morpholinecarbonyl chlorideHCID 178517744HCID 178517744, 화합물

생성물 1

HCID 69519825Morpholine-4-carboxylic Acid 4-trifluoromethyl-pyrimidin-2-yl Ester수율 80%

시약·촉매·용매 2

HCID 6228Dimethylformamide
용매
HCID 57417360Sodium chloride; water용매

실험 절차

A solution of 4-trifluoromethyl-2-hydroxypyrimidine (0.49 g, 3.00 mmol), 4-morpholinecarbonyl chloride (0.45 g, 3.00 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.34 g, 3.00 mmol) in dimethylformamide (15 ml) was stirred at room temperature for 1 hour. Water and brine were added and the solution was extracted twice with dichloromethane. The combined organic layers were dried over sodium sulphate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (30:70→50:50)) yielding the title compound (0.66 g, 80% yield) as a white solid.

후처리

  1. extractionthe solution was extracted twice with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (30:70→50:50))

출처 및 근거

ORD 기록
ord-a639b64c5605482a8a115cbb8b611c2a
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07279470B2

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