Sodium Hydroxide → N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Participants

Reaction Steps

To a mixture of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-tosyl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl)pyrimidine-2,4-diamine (400 mg, 0.80 mmol) in MeOH (5 mL) was added aqueous NaOH (2 N, 5 mL). The mixture was heated at reflux overnight. The reaction mixture was extracted with EtOAc (100 mL×3), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by preparative HPLC to afford 30 mg (6.3%) of N241H-pyrazolo[4,3-c]pyridin-4-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as yellow solid. 1H NMR (500 MHz, DMSO-d4) δ 9.44 (brs, 1H), 8.32 (brs, 1H), 8.23 (d, J=6 Hz, 1H), 7.80 (d, J=5 Hz, 1H), 7.40 (d, J=6 Hz, 1H), 6.14-5.99 (m, 2H), 4.87 (d, J=5.5 Hz, 2H), 1.80 (s, 1H), 0.88-0.87 (m, 2H), 0.66 (s, 2H); MS (ESI): m/z=348.1 [M+1]+.

Provenance & Evidence