Ammonia → (S)-2,4-Diamino-6-((1-(1-methyl-6-(thiazol-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)pyrimidine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a sealed tube were added (S)-4-amino-6-((1-(1-methyl-6-(thiazol-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile (20 mg, 0.044 mmol) in dioxane (5 mL) along with 0.5M ammonia in dioxane (0.440 mL, 0.220 mmol). The reaction mixture was heated at 60° C. overnight and then concentrated. The crude product was taken up in DMF and purified by preparative HPLC (basic mode) eluting with 30-40% ACN in water. The fractions containing the desired product were combined and concentrated in vacuo to give the title compound as an off-white solid (12 mg, 70%). 1H NMR (500 MHz, CD3OD) δ ppm 1.42 (d, J=6.83 Hz, 3 H), 3.87 (s, 3 H), 5.76 (d, J=6.83 Hz, 1 H), 6.60-6.67 (m, 1 H), 7.56 (s, 1 H), 7.76 (s, 1 H), 7.91 (d, J=0.98 Hz, 1 H), 9.16 (d, J=1.95 Hz, 1 H); ESI-MS m/z [M+H]+ calc'd for C18H17N9S, 392; found 392.

Provenance & Evidence