(Z)-1-Ethoxy-2-(tributylstannyl)ethene → HCID 69014896, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,9-dibenzyl-6,9-dihydro-6-oxo-8-bromopurine (20) (1.20 g, 3.04 mmol) bis(triphenylphosphine)palladium(II)chloride (0.213 g, 0.3 mmol) and ethoxyvinyl(tributyl)tin (2.19 g, 6.07 mmol) in dry DMF (50 mL) was heated under N2 at 70° C. for 22 h. DMF was distilled off and the resulting residue dissolved in EtOAc (100 mL) and filtered through a pad of celite. The solvent was distilled off and the residue was purified by flash chromatography (EtOAc:hexane, 6:4). Yield 0.989 g (88%). Mp 167-168° C. 1H NMR (CDCl3) δ 1.26 (t, 3H, CH3, J=7.5 Hz), 3.86 (q, 2H, CH2, J=7 Hz), 4.46 (d, 1H, CH, J=2.5 Hz), 5.26 (s, 2H, benzylic CH2), 5.32 (d, 1H, CH2 J=3 Hz), 5.60 (s, 2H, benzylic CH2), 7.10-7.37 (m, 10H, Ar—H), 7.99(s, 1H, purine C2—H). 13C NMR (CDCl3) δ 14.1, 47.8, 49.1, 63.8, 90.2, 123.5, 126.6, 126.6, 127.5, 127.5, 128.2, 128.7, 128.7, 128.9, 129.1, 129.1, 136.2, 136.7, 146.2, 146.9, 148.9, 151.9, and 156.6. FAB-HRMS: [M+H]+ calcd. for C23H23N4O2 387.1821, found 387.1815.

Provenance & Evidence