2,6-Lutidine → HCID 131730094, compound

Participants

Reaction Steps

Compound 55.5 (92 mg, 0.16 mmol) in CH3CN (3.0 mL) was treated with 2,6-lutidine (183 μL, 1.6 mmol) and TMSBr (102 μL, 0.79 mmol) at 0° C. for 30 min. The mixture was warmed to r.t. and stirred for 30 min. The mixture was cooled to −40° C. and treated with triethylamine (446 μL, 3.2 mmol) in MeOH (2 mL). The mixture was warmed to r.t. and concentrated in vacuo. The residue was dissolved in concentrated NH4OH (1.5 mL) and warmed to 60° C. The solution was stirred for 2 h and then concentrated in vacuo. The residue was subjected to reverse phase HPLC eluting with 5-50% CH3CN-water gradient to give 55.6 (26 mg, 48% yield): white solid (bis-ammonium salt); 1H NMR (D2O, 300 MHz) 8.01 (s, 1H), 7.96 (s, 1H), 6.24 (m, 2H), 6.01 (app t, J=16 Hz, 1H), 5.23 (d, J=52.2 Hz, 1H), 4.44 (m, 2H), 4.31 (m, 1H); 31P NMR (D2O 121.4 MHz) 7.7; 19F NMR (D2O, 282 MHz) −203 (m, 1F); MS (ESI) m/z 345 [M+H]+.

Provenance & Evidence