Diisopropylethylamine → 4-Amino-6-[1-(3-pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethyl amino]-pyrimidine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-(3-pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethylamine (450 mg, 2.09 mmol) and 4-amino-6-chloro-pyrimidine-5-carbonitrile (325 mg, 2.09 mmol) in n-butanol (8 mL) was added DIEA (0.6 mL, 3.01 mmol) at rt. The reaction mixture was stirred at 110° C. overnight. The mixture was concentrated in vacuo. The residue was purified by column chromatography using silica gel (100-200 mesh) and 0-60% acetone in hexane to provide 4-amino-6-[1-(3-pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethyl amino]-pyrimidine-5-carbonitrile: 1H NMR (400 MHz, DMSO-d6) δ 1.272 (d, J=6.4 Hz, 3H), 6.047-6.118 (m, 1H), 7.375 (br s, 2H), 7.446-7.477 (m, 2H), 8.022-8.060 (m, 2H), 8.230-8.280 (m, 1H), 8.400-8.490 (m, 2H), 8.727 (s, 1H), 8.878 (s, 1H). LC-MS (ESI) m/z 358.2 [M+H]+.

Provenance & Evidence