Tetrabutylammonium Hydroxide → Tetrabutylammonium

Participants

Reaction Steps

6-Iodo-9H-purin-2-amine (133 g., 510 mmole) ground up in a mortar and pestle was washed into a 2 liter pot with 1.5 liter dichloromethane. Aqueous tetrabutylammonium hydroxide (1.53M, 333 ml., 510 mmole) was added and the mixture was stirred mechanically for 30 minutes. The mixture was then filtered through Celite, washed five times with methylene chloride, and the methylene chloride layer was separated, dried (MgSO4), and evaporated. The residue was evaporated from toluene (300 ml.). The residue was taken up in 1 liter of ethyl acetate and heated briefly to form a two-phase mixture. This mixture was stirred mechanically at room temperature for 30 minutes. The resulting crystals were filtered, washed with ethyl acetate, and dried under vacuum overnight to give 213.5 g. of product. 20 g. of this material was dried further overnight at 50° C. under vacuum over phosphorus pentoxide to give 6-iodo-9H-purin-2-amine, ion (1-), tetrabutylammonium (1:1) salt; m.p. 114°-116° C.

Provenance & Evidence