Isoamyl Alcohol → 2-[(3-Methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-Purin-6-amine

Participants

Reaction Conditions

Reaction Steps

To 3-methyl-1-butanol (1.03 mL) in DME (5 mL) was added sodium tert-butoxide (912 mg) in portions over 5 mins with stirring. The mixture was stirred at room temperature until homogeneous. 2-Chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (600 mg) was added followed by DME (4.6 mL). The reaction was heated at 110° C. overnight. The reaction was allowed to cool, was taken up in water (20 mL) and washed with EtOAc (2×20 mL). The organics were extracted with brine, separated, dried over MgSO4, filtered and concentrated in vacuo to give a viscous yellow oil. The crude material was purified by C18 reverse phase chromatography (ISCO) using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluent (30-80%) to afford the title compound as a yellow residue (266 mg).

Provenance & Evidence