Reacción #61635

Ecuación de reacción

diethyl azodicarboxylate

2,6-dichloropurine

cyclopentanol

triphenyl phosphine

→

2,6-dichloro-9-cyclopentyl-9H-purine

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroEvaporate the solvent in vacuo
2. 2
   workup.ADDITIONcharge directly onto a 500 g silica gel column
3. 3
   Lavadoelute with DCM
4. 4
   Concentraciónconcentrate the desired fractions

Procedimiento

Dissolve 2,6-dichloropurine (1, 680 mg, 3.60 mmol), cyclopentanol (2a, 260 mg, 3.02 mmol), and triphenyl phosphine (950 mg, 3.60 mmol) in dry THF (20 mL) and cool to 0° C. Add diethyl azodicarboxylate (DEAD, 570 μL, 3.60 mmol) dropwise over a period of 15 minutes under a nitrogen atmosphere. Stir the resulting solution for 60 hours at room temperature. Evaporate the solvent in vacuo, charge directly onto a 500 g silica gel column, and elute with DCM and concentrate the desired fractions to give 2,6-dichloro-9-cyclopentyl-9H-purine (3a).

Fuente