Sodium Hydroxide → HCID 71611843, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (S)—N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine (120 mg, 0.226 mmol) in MeOH (10 mL) was added aqueous NaOH (18 mg, 2 mL H2O). The mixture was heated at 50° C. for 5 h. The reaction mixture was quenched by adding a sat'd, aq. NH4Cl solution and extracted with EtOAc (50 mL×3), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by preparative HPLC to afford (S)—N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(6-fluoro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)pyrimidine-2,4-diamine as white solid (25 mg, 30%). 1H NMR (500 MHz, MeOD) δ 7.79-7.81 (d, 1H), 7.53-7.59 (m, 2H), 6.62 (s, 1H), 6.03-6.27 (m, 2H), 5.54-5.59 (m, 1H), 1.95 (m, 1H), 1.59 (m, 3H), 1.01 (m, 2H), 0.78 (m, 2H); MS (ESI): m/z=379.1 [M+1]+.

Provenance & Evidence