Trifluoroacetic acid → HCID 71599599, compound

Participants

Reaction Steps

To ethyl 4-{2-methoxy-6-[(2-methylacryloyl)amino]pyridine-4-yl}-7-{[2 (trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (20 mg, 0.039 mmol) in DCM (0.50 mL) was added TFA (500 μL, 6.49 mmol) and the reaction was stirred for 2 hours at room temperature. The reaction was then concentrated in vacuo, and the residue dissolved in acetonitrile (1.0 mL) and ammonium hydroxide (1.0 mL) was added. The reaction was stirred for an additional 1 hour at room temperature before being concentrated in vacuo and purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. The products were collected and lyophilized to afford a colorless solid. LRMS calcd for C19H20N5O4[M+H]+: 382, found 382. 1H NMR (600 MHz, DMSO-D6) δ 13.08 (bs, 1H), 10.05 (s, 1H), 8.92 (s, 1H), 8.33 (d, 1H, J=3.1 Hz), 7.87 (d, 1H, J=0.9 Hz), 6.67 (d, 1H, J=1.1 Hz), 5.87 (s, 1H), 5.52 (s, 1H), 3.90 (q, 2H, J=7.2 Hz), 3.89 (s, 3H), 1.91 (s, 3H), 0.92 (t, 3H, J=7.2 Hz).

Provenance & Evidence