4-chloro-5H-pyrrolo[3,2-d]pyrimidine → [2-(benzyloxy)-5-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)phenyl]methanol

HRID 1786923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786923
Cl[C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:16]([CH2:18][OH:19])[CH:17]=1>CN(C)C=O>[CH2:21]([O:20][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:2]2[C:3]3[NH:10][CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:17][C:16]=1[CH2:18][OH:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

4

Edukt 2

HCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidineHCID 219043564-Benzyloxy-3-hydroxymethylaniline

Produkt 1

HCID 57597321[2-(benzyloxy)-5-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)phenyl]methanolAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (307 mg), [5-amino-2-(benzyloxy)phenyl]methanol (459 mg) and N,N-dimethylformamide (10 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate containing tetrahydrofuran. The extract washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→30:70). Ethanol and ethyl acetate were added and the precipitate was collected by filtration to give the title compound (279 mg) as a brown powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. additioncontaining tetrahydrofuran
  5. washThe extract washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→30:70)
  9. additionEthanol and ethyl acetate were added
  10. filtrationthe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-fad64d0f1a4e45a4b69194a647c21ad6
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507740B2

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