1-Butanol → 2-butoxy-9H-purin-6-amine

HRID 1371460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371460
[Na].[CH2:2]([OH:6])[CH2:3][CH2:4][CH3:5].Cl[C:8]1[N:16]=[C:15]2[C:11]([NH:12][CH:13]=[N:14]2)=[C:10]([NH2:17])[N:9]=1>O>[CH2:2]([O:6][C:8]1[N:16]=[C:15]2[C:11]([NH:12][CH:13]=[N:14]2)=[C:10]([NH2:17])[N:9]=1)[CH2:3][CH2:4][CH3:5]

Komponenten

5

Edukt 3

HCID 2631-ButanolHCID 949042-ChloroadenineHCID 5360545Sodium2×

Produkt 1

HCID 229289002-butoxy-9H-purin-6-amineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

Sodium (13.6 g, 0.59 mol) was added to butanol (480 ml), the temperature of the mixture was raised to 90° C. to completely dissolve sodium therein. Subsequently, 2-chloroadenine (4.0 g, 23.6 mmol) was added, and the resultant was heated under reflux for 9 hours. After the reaction solution was cooled to 4° C., water (400 ml) was added thereto, and the resultant was vigorously stirred for 30 minutes. The separated layer of butanol was concentrated under reduced pressure, water (400 ml) was added to the residue, and concentrated hydrochloric acid was added dropwide under ice cooling to neutralize the product. The precipitated solid was collected by filtration, the resulting solid was added to ethanol (70 ml), and the resultant was heated under reflux for 30 minutes. The product was cooled to room temperature, and the precipitated solid was then collected by filtration. Thus, 3.72 g of the title compound was obtained (yield: 76%).

Aufarbeitung

  1. temperaturethe resultant was heated
  2. temperatureunder reflux for 9 hours
  3. concentrationThe separated layer of butanol was concentrated under reduced pressure, water (400 ml)
  4. additionwas added to the residue, and concentrated hydrochloric acid
  5. additionwas added dropwide under ice cooling
  6. filtrationThe precipitated solid was collected by filtration
  7. additionthe resulting solid was added to ethanol (70 ml)
  8. temperaturethe resultant was heated
  9. temperatureunder reflux for 30 minutes
  10. temperatureThe product was cooled to room temperature
  11. filtrationthe precipitated solid was then collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-9d611ed16734465fa117b6a74406ec3b
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157465B2

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