N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine

Chemical properties

White crystals

The Uses of N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine

N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine is a highly mobile synthetic cytokinin. Foliar spray of N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine increased branching in carnation, chrysan-themum, pointsettia, petunia and fuchsia. Application of N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine to flower buds at an early stage increased both the diameter and the fresh weight of carnation flowers or chrysanthemum infloresences.

Preparation

Dissolve alcohol in PrOH (14 ml). Add TEA (0.95 ml, 6.9 mmol) and 6-chloro-9-(tetrahydropyran-2-yl)purine (1.64 g) to the reaction mixture. Heat the reaction mixture at 45 °C for 6 hours. Cool the reaction mixture. Filter the mixture. Evaporate the filtrate partly. Purify the filtrate by CC (60.3 g of silica gel, mobile phase CHCl3-Me2CO 4:1, flow rate 7.5 ml/min). The product is a light yellow viscous substance that starts to crystallize after two weeks of drying over P2O5 in a vacuum desiccator.
Figure Preparation of N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine

Safety Profile

Moderately toxic by ingestion.Experimental reproductive effects. When heated todecomposition it emits toxic vapors of NOx.