Hydrochloric Acid → HCID 11300941, compound

Participants

Reaction Conditions

Reaction Steps

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%

Provenance & Evidence