Reacción #10550

Ecuación de reacción

N-(1-benzyl-4-piperidinyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide

ammonium formate

→

6-[(2,2-Diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-N-(4-piperidinyl)-9H-purine-2-carboxamide

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux for 3 hours
2. 2
   OtroThe catalyst was removed by filtration through Arbocel (trade mark), solvent
3. 3
   Otroremoved by evaporation under reduced pressure
4. 4
   Otrothe residue purified by column chromatography on silica gel eluting with a gradient system of dichloromethane
5. 5
   OtroAfter evaporation of appropriate fractions the target compound
6. 6
   Otrowas obtained as a white solid, (0.6 g, 67%)

Procedimiento

A solution of N-(1-benzyl-4-piperidinyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide (Preparation 33) (1.03 g, 1.47 mmol), palladium (II) hydroxide (0.9 g) and ammonium formate (0.46 g, 7.3 mmol) in ethanol (10 ml) was heated under reflux for 3 hours. The catalyst was removed by filtration through Arbocel (trade mark), solvent removed by evaporation under reduced pressure and the residue purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:concentrated aqueous ammonia (90:10:1, by volume) changing to dichloromethane: methanol:concentrated aqueous ammonia (80:20:2, by volume). After evaporation of appropriate fractions the target compound was obtained as a white solid, (0.6 g, 67%).

Fuente