Propargyl alcohol → HCID 178456481, compound

Participants

Reaction Steps

A solution of 4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)-bicyclo-[2.2.2]octane-1-carbaldehyde oxime (87 mg, 0.22 mmol) and N-chloro succinimide (1.2 eq, 0.27 mmol, 36 mg) in DMF (6 ml) was heated in an oil bath at 60° C. for 1.5 h. The reaction flask was removed from the bath and allowed to cool to rt and propargyl alcohol (2.0 eq, 0.44 mmol, 25 mg) was added. The flask was returned to the oil bath, Et3N (2.0 eq, 0.44 mmol, 44 mg) was added over a period of 15 minutes and the resulting mixture was heated at 60° C. for 3.5 h. The cool reaction mixture was evaporated in vacuo to afford a solid residue that was purified by radial chromatography (2 mm plate) using a gradient of 2-10% MeOH in CH2Cl2 as eluent. Product-containing fractions were combined and concentrated to afford 31 mg (26%) of a white solid. MS: 442 (MH+).

Provenance & Evidence