Ammonia → Adenine

Temperature

60 °C

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.

1. customEvaporation in vacuo and twice repetition with toluene
2. customgave the crude 6-chloro intermediate, which
3. filtrationAfter 3.5 hr the solid was filtered off
4. customthe solution evaporated in vacuo to dryness
5. dissolutionThe residue was dissolved in dichloromethane
6. extractionextracted with 1 n NaOH
7. customevaporated again to dryness
8. dissolutionThe residue was dissolved in 20 ml of methanol
9. additiontreated with 2.9 ml of 1 m methanolic HCl
10. customevaporated to dryness
11. customCrystallization from ethyl acetate

ORD record

ord-ed9d41b64a2e4eca8c87e570ea48c06d

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06413975B1