1H-Indazol-5-amine → N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1H-indazol-5-yl)pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (200 mg, 0.8 5 mmol, 1 equiv.) and 1H-indazol-5-amine (340 mg, 2.55 mmol, 3 equiv.) in 1,4-dioxane (1 ml) and n-BuOH (0.5 ml) was heated to 100° C. The mixture was allowed to react overnight (about 15 hr). The mixture was filtered under reduced pressure to afford title compound N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1H-indazol-5-yl)pyrimidine-2,4-diamine (Compound 13) (44.5 mg, 15.8%) as solid. LC-MS (m/z)=333.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.44 (s, J=17.7 Hz, 2H), 0.82 (t, J=17.7 Hz, 2H), 1.758 (s, 1H), 6.02 (s, 1H), 6.41 (s, 1H), 7.46 (d, J=8.7 Hz, 1H), 7.56 (d, J=9 Hz, 1H), 7.92 (d, J=6.6 Hz, 1H), 8.04 (d, J=9.6 Hz, 2H), 9.71 (s, 1H), 10.38 (s, 1H), 11.77 (s, 1H), 13.05 (s, 1H).

Provenance & Evidence