Triethylamine → (2S)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione

Participants

Reaction Steps

To a solution of 4-[(1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethyl]-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one (1 g, 2.74 mmol) in CHCl3 (50 mL) was added Et3N (0.953 mL, 6.84 mmol) followed by a solution of methanesulfonic anhydride (0.953 g, 5.47 mmol) in CHCl3 (50 mL). The reaction mixture was stirred at reflux temperature for 5 h. The crude of reaction was diluted with water, washed with NaCl, dried (MgSO4), filtered, and concentrated. Purification by flash chromatography using a 40 g silica gel cartridge, and mixtures of DCM and MeOH as eluent afforded (2S)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione (0.806 g, 88%) as a tan solid.

Provenance & Evidence