Acetic Acid → 8-chloro-3-(4-fluorobutyl)-3,7-dihydro-1H-purine-2,6-dione

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Reaction Steps

To a suspension of 8-chloro-3-(4-fluorobutyl)-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.33 mmol, 1eq) in anhydrous DCM (2 ml) was added palladium tetrakis (38 mg, 0.033 mmol, 10% bw), followed by acetic acid (115 ul, 121 mg, 2.01 mmol, 6eq) and phenyl silane (410 ul, 360 mg, 3.33 mmol, 10eq). The resulting light yellow solution was stirred at ambient temperature for 16 h to give a dark purple solution. The solvent was removed under a stream of nitrogen and the residue dissolved in a DMSO/methanol solution (3 ml, 2:1) with heating. The gelatinous mixture was allowed to cool to ambient temperature, filtered then purified by mass directed autopreparative HPLC to give the title compound as a white solid (35 mg, 43%). m/z 261.2[MH+] NMR (400 MHz, MeOD), δH 4.45 (2H, dt, J=47 and 6 Hz), 4.03 (2H, t, J=7 Hz), 1.90-1.65 (4H, m).

Provenance & Evidence