تفاعل #43571

معادلة التفاعل

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

المذيبات

2-Propanol

ظروف التفاعل

المعالجة

1. 1
   أخرىequipped with mechanical stirrer, gas inlet, gas outlet
2. 2
   درجة الحرارةreflux condenser
3. 3
   درجة الحرارةThe mixture was heated
4. 4
   درجة الحرارةto reflux
5. 5
   أخرىthe progress of the reaction by TLC analysis
6. 6
   أخرىthe heat source was removed
7. 7
   درجة الحرارةThe suspension was cooled
8. 8
   workup.STIRRINGunder stirring in an ice-bath for 1.5 to 2 hours
9. 9
   أخرىThe solids were isolated by vacuum filtration
10. 10
    غسيلwashed with ice-cold 2-propanol
11. 11
    تجفيفThe 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

الإجراء التجريبي

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%.

المصدر