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3-Chloro-4-(2-pyridylmethoxy)aniline → ethyl 5-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]-2-furoate

HRID 1925973
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1925973
Cl[C:2]1[C:3]2[N:10]([CH2:11][C:12]3[O:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)[NH2:26]>CN1CCCC1=O.C(=O)([O-])O.[Na+]>[Cl:22][C:23]1[CH:24]=[C:25]([NH:26][C:2]2[C:3]3[N:10]([CH2:11][C:12]4[O:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:13]=4)[CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:27]=[CH:28][C:29]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1
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Komponenten

5

Edukt 2

HCID 167812123-Chloro-4-(2-pyridylmethoxy)anilineHCID 86615753ethyl 5-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]-2-furoate

Produkt 1

HCID 57597254ethyl 5-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]-2-furoateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel
HCID 516892
Sodium Bicarbonate
Lösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of ethyl 5-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]-2-furoate (300 mg) in 1-methyl-2-pyrrolidone (2.0 mL) was added 3-chloro-4-(pyridin-2-ylmethoxy)aniline (360 mg), and the mixture was heated to 140° C. and stirred for 1.5 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodium hydrogen carbonate solution (30 mL) and extracted with a mixed solvent (45 mL×3) of ethyl acetate/tetrahydrofuran (1/1). The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (basic silica gel, eluent:ethyl acetate/methanol=10/0→8/2). The object fraction was concentrated under reduced pressure. Chloroform/diisopropyl ether (1/9) was added to the residue, and the resultant precipitate was collected by filtration and dried under reduced pressure to give the title compound (440 mg) as pale-yellow powder crystals.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionextracted with a mixed solvent (45 mL×3) of ethyl acetate/tetrahydrofuran (1/1)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe object fraction was concentrated under reduced pressure
  7. additionChloroform/diisopropyl ether (1/9) was added to the residue
  8. filtrationthe resultant precipitate was collected by filtration
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-13fd3d33cde84617b199b9fc9cbff0e6
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08178543B2

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