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

HRID 1021266
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1021266
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

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

Produkt 1

HCID 86686214Ethyl 2-fluoro-3-({[2-(morpholin-4-yl)pyrimidin-5-yl]oxy}methyl)benzoateAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-496f576c673e4153ad79fa8601bdf548
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08716470B2

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