Ethynyltributyltin → 2-[(S)-1-phenylethylamino]-4-[6-(4-tributylstannyl-triazol-1-yl)benzimidazol-1-yl]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A solution containing 95 mg of 2-[(S)-1-phenylethylamino]-4-[6-azidobenzimidazol-1-yl]pyrimidine and 386 μL tributyl-ethynylstannane in 2 mL 1,4-dioxane was stirred at 100° C. for 48 hours under 1 atm of nitrogen. The solution was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with methanol in methylene chloride to give 139 mg of the title compound. RF: 0.4 (5% MeOH in CH2Cl2). 1H NMR (500 MHz, CD3OD): δ0.91 (t, J=7.4 Hz, 3H), 1.25 (t, J=8.1 Hz, 2H), 1.39 (m, 2H), 1.57 (d, J=6.9 Hz, 3H), 1.65 (m, 2H), 5.22 (q, J=7.1 Hz, 1H), 7.03 (d, J=5.5 Hz, 1H), 7.0-7.4 (m, 5H), 7.76 (m, 1H), 7.85 (d, J=8.7 Hz, 1H), 8.35 (d, J=5.3 Hz, 1H), 8.50 (s, 1H), 8.91 (m, 2H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 673.2 (M+1).

Provenance & Evidence