Trimethylsilylacetylene → HCID 86745213, compound

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').

1. customThe title compound was prepared in a manner analogous to the procedure
2. customdeoxygenated triethylamine (50 mL)
3. customThe reaction was evaporated to dryness
4. dissolutionthe residue dissolved in CHCl3
5. washThe CHCl3 was washed with 5% EDTA (2×25 mL)
6. dry with materialby drying over Na2SO4
7. filtrationThe CHCl3 solution was filtered
8. customevaporated to a solid which
9. dissolutionwas dissolved in 0.5N NaOCH3 in MeOH (50 mL) at ambient temperature
10. filtrationDOW 50 H+, filtered
11. customevaporated in vacuo
12. customThe residue was chromatographed on silica gel
13. washeluted with 9:1 CHCl3/MeOH (v/v)
14. customCombination and evaporation of the appropriate fractions

ORD record

ord-dbb962597230484c8a3547b3c5d70b6b

Source dataset

uspto-grants-1991_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05064946