Triphenylphosphine → 3-Butyl-8-chloro-1-{3-[5-(phenylmethyl)-1,2,4-oxadiazol-3-yl]propyl}-3,7-dihydro-1H-purine-2,6-dione

Participants

Reaction Steps

A solution of 3-[5-(phenylmethyl)-1,2,4-oxadiazol-3-yl]-1-propanol (594 mg, 2.7 mmol) in THF (25 ml) was treated with 3-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (700 mg, 2.48 mmol) and PPh3 (779 mg, 2.97 mmol) under nitrogen. DBAD (684 mg, 2.97 mmol) was added in one portion and the reaction left to react for 60 h. The mixture was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated. MeOH was added to the residue and then passed down an aminopropyl column with the product eluting with 2-4% AcOH/MeOH. Product fractions were combined and concentrated. The off-white residue was recrystallised from EtOAc:cyclohexane (1:1), giving the title compound as a white solid (696 mg, 63%).

Provenance & Evidence