Ammonia → HCID 73053997, compound

Participants

Reaction Steps

A 7 N solution of ammonia (1 mL, 7.00 mmol) in MeOH was added to (S)-2,5-dichloro-N-(1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidin-4-amine (20 mg, 0.050 mmol) while stirring at room temperature. The reaction mixture was stirred at room temperature for 1 hour and then at 100° C. in a microwave reactor for 1 hour. The mixture was concentrated, dissolved in dioxane (1 mL), and treated with ammonium hydroxide (1 mL, 7.19 mmol). The mixture was heated at 100° C. in a microwave reactor for 12 hours. The reaction was concentrated and purified by preparative HPLC (basic mode, 25% to 50% ACN/water gradient) to give the title compound as an off-white solid (13.7 mg, 72.0%). 1H NMR (500 MHz, CD3OD) δ ppm 1.42 (d, J=6.35 Hz, 3 H), 3.66 (s, 3 H), 3.90 (s, 3 H), 5.46 (q, J=6.51 Hz, 1 H), 6.45-6.49 (m, 1 H), 6.69-6.72 (m, 1 H), 7.65 (d, J=2.93 Hz, 2 H), 7.69 (s, 1 H), 7.84 (s, 1 H); ESI-MS m/z [M+H]+ calc'd for C18H19ClN8, 383.14; found 383.3.

Provenance & Evidence