Hydrochloric Acid → HCID 11300941, compound

Temperature

38.5 °C

8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.442 mmol) was stirred with sodium carbonate (52 mg, 0.486 mmol) in dry DMF (3 ml) for 30 min. Cyclohexylethyl bromide (93 mg, 0.486 mmol) was added, and the mixture was stirred at 37-40° C. under nitrogen for 65 h, followed by heating at 90° C. for 18 h. After cooling, the solution was degassed by evacuating and introducing nitrogen several times, and tetrakis(triphenylphosphine)palladium(0) (76 mg, 0.066 mmol) and morpholine (0.385 ml, 4.42 mmol) were added and the mixture stirred for 18 h. A further quantity of tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.043 mmol) and morpholine (0.2 ml) were added and stirring continued for a further 1 h. Ethyl acetate and 2M aqueous HCl were added (ca. 10 ml each) and the organic layer separated, washed with brine and evaporated. The residue was dissolved in THF and loaded onto a 5 g aminopropyl SPE cartridge. The cartridge was washed with THF followed by MeOH, and the acidic product eluted with AcOH in MeOH (5% rising to 10%). The product thus obtained was further purified by autoprep HPLC to provide the title compound, 5.5 mg, 3%

1. temperatureby heating at 90° C. for 18 h
2. temperatureAfter cooling
3. customthe solution was degassed
4. customby evacuating
5. additionwere added
6. stirringthe mixture stirred for 18 h
7. stirringstirring
8. waitcontinued for a further 1 h
9. customthe organic layer separated
10. washwashed with brine
11. customevaporated
12. dissolutionThe residue was dissolved in THF
13. washThe cartridge was washed with THF
14. washthe acidic product eluted with AcOH in MeOH (5% rising to 10%)
15. customThe product thus obtained
16. customwas further purified by autoprep HPLC

ORD record

ord-c7644035528642f8a0d4ff29b35aaa2f

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394808B2