Trimethylsilylacetylene → HCID 86745213, compound

Participants

Reaction Steps

The title compound was prepared in a manner analogous to the procedure described in (1). 5'-Acetyl-3'-azido-2',3'-dideoxy-5-iodouridine (0.4 g, 0.94 mMol) was dissolved in anhydrous, deoxygenated triethylamine (50 mL) and treated with trimethylsilyl acetylene (0.37 g, 3.8 mMol), bis(triphenylphosphine)palladium(II)chloride (14 mg), and CuI (14 mg) at 55° C. under N2 for 4 hours. The reaction was evaporated to dryness and the residue dissolved in CHCl3. The CHCl3 was washed with 5% EDTA (2×25 mL) then H2O (1×25 mL) followed by drying over Na2SO4. The CHCl3 solution was filtered and evaporated to a solid which was dissolved in 0.5N NaOCH3 in MeOH (50 mL) at ambient temperature. After 1 hour the solution was neutralized DOW 50 H+, filtered and evaporated in vacuo. The residue was chromatographed on silica gel and eluted with 9:1 CHCl3/MeOH (v/v). Combination and evaporation of the appropriate fractions yields the title compound as a solid, 80 mg(0.29 mMol, 30%): mp=134°-136° C.; UV(nm): at pH 1 λmax=286,225(ε=11300,10700), λmin=251(ε=3100); at pH 13 λmax=282(ε=9700), λmin=255(ε=5000); H NMR(DMSO-d6) δ11.6(s,1H,--NH), 8.26(s,1H,H6), 6.01(t,1H,H1',J=6.01 Hz), 5.35-5.30(m,1H,5'OH), 4.4-4.3(m,1H,H3'), 4.08(s,1H,C CH), 3.85-3.80(m,1H,H4'), 3.7-3.6(m,2H,H5'), 2.5-2.3(m,2H,H2').

Provenance & Evidence