Reaktion #487514

Reaktionsgleichung

6-Benzyloxypurine

potassium carbonate

bromoacetic acid methyl ester

→

Methyl (6-(Benzyloxy)purin-9-yl)acetate

Lösungsmittel

DMF

butanol acetic acid water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeUpon completion, the reaction mixture was partitioned between water (600 ml) and ethyl acetate (600 ml)
2. 2
   TrocknenThe organic phase was dried over magnesium sulfate
3. 3
   Sonstigeevaporated to a volume of ˜10 ml
4. 4
   Sonstigeprecipitated with pet. ether
5. 5
   SonstigeThe two products were separated by column chromatography
6. 6
   SonstigeThe products were precipitated in pet. ether

Vorschrift

6-Benzyloxypurine (4.18 g; 18.5 mmol) was added to a suspension of potassium carbonate (3.1 g; 22.4 mmol) in DMF (100 ml). After 15 min., bromoacetic acid methyl ester (1.93 ml; 20.4 mmol) was added. The reaction was monitored by TLC in butanol:acetic acid:water 4:1:1. Upon completion, the reaction mixture was partitioned between water (600 ml) and ethyl acetate (600 ml). The organic phase was dried over magnesium sulfate and evaporated to a volume of ˜10 ml and precipitated with pet. ether. The two products were separated by column chromatography using ethyl acetate as the solvent. The products were precipitated in pet. ether. Yield: 2.36 g (43%). Melting point: 111.5-115° C. UV λmax=250 nm (9-alkylated); λmax=260 nm (7-alkylated). 1H-NMR (DMSO-d6): 8.60 (1H, s); 8.43 (1H, s); 7.6-7.35 (5H, m); 5.69 (2H, s); 5.26 (2H, s); 3.75 (3H, s).

Quelle