1-Propanol → Purine, 2-amino-6-propoxy-

Participants

Reaction Conditions

Reaction Steps

Sodium (0.68 g, 29.5 mmol Aldrich lot #9621CL) was added in portions to anhydrous propanol (25 mL). Upon complete dissolution 2-amino-6-chloropurine (1 g, 5.9 mmol, Sigma lot #69F4064) was added and the reaction heated in an 85° C. oil bath under a nitrogen atmosphere for 20 hours. The solution was cooled and neutralized with Dowex 50W×12 (H+ form) (BioRad, 140-270 mesh), an acidic ion exchange resin. The resin was filtered, the filtrate collected and adsorbed onto silica gel column and eluted with CHCl3 /MeOH (9:1, v/v). Combination and evaporation of appropriate fractions gave 0.89 g of slightly impure material. Adsorption of this material onto silica gel followed by elution with EtOAc/MeOH (10:1, v/v) gave, after evaporation of combined product fractions, 0.76 g, (3.9 mmol; 67%). mp=198°-200° C.

Provenance & Evidence