Ammonia → Adenine

Participants

Reaction Conditions

Reaction Steps

1.27 g (2.8 mM) of the above hypoxanthine (C.) was heated in 13 ml of phosphorus oxychloride to 70° C. for 30 min. Evaporation in vacuo and twice repetition with toluene gave the crude 6-chloro intermediate, which was dissolved in 40 ml of THF and added at 0-5° C. to 12 ml of 32% aqueous ammonia. After the addition of 50 g of liquid ammonia the solution was heated to 60° C. in a 450 ml pressure reactor (340 psi). After 3.5 hr the solid was filtered off and the solution evaporated in vacuo to dryness. The residue was dissolved in dichloromethane, extracted with 1 n NaOH and evaporated again to dryness. The residue was dissolved in 20 ml of methanol, treated with 2.9 ml of 1 m methanolic HCl and evaporated to dryness. Crystallization from ethyl acetate gave 1.24 g (90.5%) of title adenine with mp 172-175° C.

Provenance & Evidence