1,1,1-Trimethoxybutane → HCID 178439946, compound

Participants

Reaction Steps

A mixture of 6-(benzyloxy)-N2-phenylpyridine-2,3-diamine (90 mg, 0.31 mmol), trimethyl orthobutyrate (5 mL), and TFA (20 μL) was stirred at room temperature for 2 h. The mixture was concentrated in vacuo and the residue dissolved in MeOH (5 mL). Palladium on carbon (20% wt./wt., 15 mg,) was added and the mixture was stirred vigorously under H2 (1 atm) for 1 h. The mixture was filtered through Celite® and concentrated to give the title compound as a white solid (26 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.85 (t, J=7.6 Hz, 3H), 1.65 (s, J=7.3 Hz, 2H), 2.62 (t, J=7.6 Hz, 2H), 6.51 (d, J=8.6 Hz, 1H), 7.45-7.56 (m, 3H), 7.60 (t, J=7.6 Hz, 2H), 7.87 (d, J=8.3 Hz, 1H), 10.75 (br s, 1H).

Provenance & Evidence