Sodium Methoxide → 2-[(2-Cyclopropylethyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1010978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010978
Br[C:2]1[N:3]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH2:13][CH2:14][CH:15]1[CH2:17][CH2:16]1)[N:5]=2.[CH3:24][O-:25].[Na+]>CO>[CH:15]1([CH2:14][CH2:13][O:12][C:6]2[N:5]=[C:4]3[C:9]([N:10]=[C:2]([O:25][CH3:24])[N:3]3[CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[C:8]([NH2:11])[N:7]=2)[CH2:17][CH2:16]1

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 576996678-Bromo-2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Produkt 1

HCID 576996292-[(2-Cyclopropylethyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 8-bromo-2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.867 g) in dry MeOH (14 mL) was treated with sodium methoxide solution (3.1 mL, 25 wt. MeOH) and was heated to reflux for 5 h. The reaction was concentrated under reduced pressure before being partitioned between EtOAc (100 mL) and ammonium chloride (100 mL). The organics were separated and aqueous was re-extracted with EtOAc (100 mL). The combined organics were washed with brine (100 mL), separated and dried using a hydrophobic frit. The organics were evaporated under reduced pressure to give the title compound as a brown foam (845 mg).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. concentrationThe reaction was concentrated under reduced pressure
  4. custombefore being partitioned between EtOAc (100 mL) and ammonium chloride (100 mL)
  5. customThe organics were separated
  6. extractionaqueous was re-extracted with EtOAc (100 mL)
  7. washThe combined organics were washed with brine (100 mL)
  8. customseparated
  9. customdried
  10. customThe organics were evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3fd0a6ae56f94434bebe3ceb1b1d3a34
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977344B2

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