Reacción #67399

Ecuación de reacción

Ethyl 2-formyl-3-oxopropionate

2-hydrazinoadenosine

→

Ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate

Disolventes

2-Propanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped with mechanical stirrer, gas inlet, gas outlet
2. 2
   Temperaturareflux condenser
3. 3
   TemperaturaThe mixture was heated
4. 4
   Temperaturato reflux
5. 5
   Otrothe progress of the reaction by TLC analysis
6. 6
   Otrothe heat source was removed
7. 7
   TemperaturaThe suspension was cooled
8. 8
   workup.STIRRINGunder stirring in an ice-bath for 1.5 to 2 hours
9. 9
   OtroThe solids were isolated by vacuum filtration
10. 10
    Lavadowashed with ice-cold 2-propanol
11. 11
    SecadoThe product, ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate, was dried under reduced pressure to a constant weight

Procedimiento

Ethyl 2-formyl-3-oxopropionate (23.93 g, 0.17 mol) was placed in a flask equipped with mechanical stirrer, gas inlet, gas outlet and reflux condenser. 2-Propanol was added to the flask followed by 2-hydrazinoadenosine (44.45 g, 0.15 mol). The mixture was heated to reflux under stirring for 2-4 hours, following the progress of the reaction by TLC analysis. When the reaction was judged complete, the heat source was removed and the mixture cooled to room temperature. The suspension was cooled under stirring in an ice-bath for 1.5 to 2 hours. The solids were isolated by vacuum filtration, and washed with ice-cold 2-propanol. The product, ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate, was dried under reduced pressure to a constant weight. Yield 54.29 g, purity (by HPLC) 96.6%.

Fuente