N,N-Dimethylaniline → 1H-Purine, 6-chloro-, monohydrochloride

Participants

Reaction Steps

A mixture of 50 g (0.368 mole) of hypoxanthine, 120 ml. of N,N-dimethylaniline and 500 ml. of phosphorus oxychloride was refluxed for 20 minutes. Excess phosphorus oxychloride was removed by vacuum distillation with an external oil bath having a temperature below 70° C. and 1.0 liter of methylene chloride was added to the red oily residue. The red methylene chloride solution was cooled in an ice water bath and hydrogen chloride gas was bubbled through the solution until the solution turned a bright yellow color. After stirring the reaction mixture overnight, nitrogen was passed through the solution for 1.5 hours to remove excess hydrogen chloride. The product was collected by filtration, washed with two 150 ml. portions of hot methylene chloride and dried to give 59.3 g (99% yield) of 6-chloropurine hydrochloride, as a cream colored solid, λ max (H2O)=264 nm, ε=9.32×103.

Provenance & Evidence