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Acetonitrile → Ethyl 2-fluoro-3-({[2-(morpholin-4-yl)pyrimidin-5-yl]oxy}methyl)benzoate

HRID 2171665
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HRID 2171665 반응식
[N:1]1([C:7]2[N:12]=[CH:11][C:10]([OH:13])=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:15][C:16]1[C:17]([F:27])=[C:18]([CH:24]=[CH:25][CH:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20].CC#N.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C1COCC1>[F:27][C:17]1[C:16]([CH2:15][O:13][C:10]2[CH:11]=[N:12][C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[N:8][CH:9]=2)=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 198710352-(4-morpholinyl)-5-PyrimidinolHCID 58009396Ethyl 3-(bromomethyl)-2-fluorobenzoate

생성물 1

HCID 86686214Ethyl 2-fluoro-3-({[2-(morpholin-4-yl)pyrimidin-5-yl]oxy}methyl)benzoate수율 63.2%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8028Tetrahydrofuran용매

실험 절차

2-(Morpholin-4-yl)pyrimidin-5-ol (300 mg) and ethyl 3-(bromomethyl)-2-fluorobenzoate (850 mg) were mixed with MeCN (5 ml), THF (2 ml) and DMF (1 ml), and potassium carbonate was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and EtOAc and water were then added thereto. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain ethyl 2-fluoro-3-({[2-(morpholin-4-yl)pyrimidin-5-yl]oxy}methyl)benzoate (378 mg).

후처리

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and EtOAc and water
  3. additionwere then added
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-4e40dc1db5a749588bc0d78723f0e6f8
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051283B2

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