Reaktion #83791

Reaktionsgleichung

3-amino-6-methoxy-2-methylaminopyridine

glycolic acid

toluene

water

→

title compound

2-Hydroxymethyl-5-methoxy-3-methyl-3H-imidazo[4,5-b]pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 4 hours
2. 2
   Extraktionafter which it was extracted with ethyl acetate
3. 3
   WaschenThe extract was washed with an aqueous solution of sodium chloride
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Sonstigeafter which the solvent was removed by distillation under reduced pressure
6. 6
   SonstigeThe residue was purified by column chromatography through silica gel
7. 7
   workup.ADDITIONby volume mixture of ethyl acetate and methanol as the eluent

Vorschrift

A solution of 2.20 g of 3-amino-6-methoxy-2-methylaminopyridine (prepared as described in Preparation 68) and 3.30 g of glycolic acid in 40 ml of toluene was heated under reflux for 4 hours. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 30:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 620 mg of the title compound, melting at 138°-140° C.

Quelle