Adenine → 2-(6-Aminopurin-9-yl)ethanol

HRID 1716369

Reaktionsgleichung

Reaktionsgleichung von HRID 1716369
N1C(N)=C2C(N=CN2)=NC=1.[CH:11]1[N:16]=[C:15]([NH2:17])[C:14]2[N:18]=[CH:19][N:20]([CH2:21][CH2:22][O:23]CP(O)(O)=O)[C:13]=2[N:12]=1.CC(C)[O-].[Mg+2].CC(C)[O-].C1(=O)OCCO1>CN(C=O)C.[OH-].[Na+].C1(C)C=CC=CC=1>[OH:23][CH2:22][CH2:21][N:20]1[CH:19]=[N:18][C:14]2[C:13]1=[N:12][CH:11]=[N:16][C:15]=2[NH2:17]

Komponenten

8

Edukt 4

HCID 190Adenine2×HCID 7303Ethylene carbonateHCID 60172AdefovirHCID 10197750Magnesium dipropan-2-olate

Produkt 1

HCID 2426522-(6-Aminopurin-9-yl)ethanolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 14798Sodium HydroxideKatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Adenine to PMEA using Magnesium Isopropoxide. To a suspension of adenine (16.8 g, 0.124 mol) in DMF (41.9 ml) was added ethylene carbonate (12.1 g, 0.137 mol) and sodium hydroxide (0.100 g, 0.0025 mol). The mixture was heated at 130° C. overnight. The reaction was cooled to below 50° C. and toluene (62.1 ml) was added. The slurry was further cooled to 5° C. for 2 hours, filtered, and rinsed with toluene (2×). The wet solid was dried in vacuo at 65° C. to yield 20.0 g (90%) of 9-(2-hydroxyethyl)adenine as an off-white solid. Mp: 238-240° C.

Aufarbeitung

  1. temperatureThe reaction was cooled to below 50° C.
  2. temperatureThe slurry was further cooled to 5° C. for 2 hours
  3. filtrationfiltered
  4. washrinsed with toluene (2×)
  5. customThe wet solid was dried in vacuo at 65° C.

Quellen und Nachweise

ORD-Eintrag
ord-c4d6bdc64e234fbeb6a77f5991defeda
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803788B2

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