Hydrochloric Acid → HCID 59395591, compound

Participants

Reaction Conditions

Reaction Steps

To 3-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (99 mg, 0.35 mmol) in dry DMF (2 ml) was added cesium carbonate (137 mg, 0.42 mmol) followed by a solution in dry DMF (1 ml) of 2-(3-chloropropyl)-5-(phenylmethyl)-1,3,4-oxadiazole (99 mg, 0.42 mmol). The mixture was stirred under nitrogen and heated at 55° C. for 2.5 h then stirred at room temperature overnight. The mixture was degassed by repeatedly evacuating and admitting nitrogen and then tetrakis(triphenylphosphine)palladium(0) (81 mg, 0.07 mmol) and morpholine (0.305 ml, 3.5 mmol) were added and stirring was continued for 5 h EtOAc and 2M HCl were added and the mixture stirred for 20 min then filtered. The organic phase was separated and evaporated, and the product was purified by aminopropyl SPE (5 g) washing with THF-MeOH (1:1) then with MeOH and eluting the acidic product with DCM-MeOH (1:1) containing 5% added AcOH. The product thus obtained was purified further by MDAP to yield the title compound (92 mg).

Provenance & Evidence