Hydrochloric Acid → HCID 58169282, compound

Participants

Reaction Steps

To N4-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(pyridin-2-yl)pyrimidine-4,5-diamine (0.88 g, 0.003 mmol, 1 equiv.) in conc.HCl (3 mL) at ice-bath was added NaNO2 (0.23 g, 0.0033 mmol, 1.1 equiv.). After 1 h, CuCl (0.33 g, 0.0033 mmol, 1.1 equiv.) in conc.HCl (6 mL) was added at 0° C. After 30 min, the reaction mixture was allowed to stand at room temperature for further 3 h, poured into ice water and adjusted to pH10 with Na2CO3, extracted with EA (50 mL×3). The organic phase was combined, dried (Na2SO4), purified with silicon chromatography (EA: PE=2:1) to produce 5-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(pyridin-2-yl)pyrimidin-4-amine (Compound 182) (0.47 g, 50%). LC-MS (m/z)=313 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.75-0.78 (m, 2H), 0.97-1.02 (m, 2H), 1.96-2.02 (m, 1H), 6.44-6.45 (m, 1H), 7.92-7.93 (m, 1H), 8.44 (s, 2H), 8.73 (d, J=2.8 Hz, 1H), 8.87 (d, J=3.6 Hz, 1H), 10.20 (bs, 1H)

Provenance & Evidence