تفاعل #574464

معادلة التفاعل

cyclopentylmethyl bromide

3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine

NaH

→

1-cyclopentylmethyl-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d] -pyrimidin-4-amine

المردود 26.4%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was cooled to 0° C.
2. 2
   درجة الحرارةThe reaction mixture was warmed to room temperature
3. 3
   workup.STIRRINGstirred for 50 hours
4. 4
   أخرىThe solvent was removed in vacuo
5. 5
   workup.ADDITIONthe yellow slurry was added to water (100 ml)
6. 6
   ترشيحA tan solid was collected by filtration
7. 7
   أخرىpurified by column chromatography on silica eluting with ether/ethanol/water (97.5/2/0.5)
8. 8
   أخرىfollowed by recrystallization from cyclohexane

الإجراء التجريبي

To a solution of 3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine (6.0 g, 0.027 mol) in DMF (50 ml) at 0° C. was added 60% NaH/mineral oil dispersion (1.06 g, 0.027 mol) in one portion. The reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was cooled to 0° C. and cyclopentylmethyl bromide (4.3 g, 0.027 mol) was added dropwise over 5 minutes. The reaction mixture was warmed to room temperature and stirred for 50 hours. The solvent was removed in vacuo, the yellow slurry was added to water (100 ml) and acidified with acetic acid. The resulting paste was stripped to dryness and the residue was slurried with ethanol. A tan solid was collected by filtration and purified by column chromatography on silica eluting with ether/ethanol/water (97.5/2/0.5) followed by recrystallization from cyclohexane to afford 2.2 g (26%) of 1-cyclopentylmethyl-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d] -pyrimidin-4-amine, m.p. 177°-178° C.

المصدر