Diisopropylethylamine → 4-Amino-6-[1-(3-pyridin-2-yl-imidazo[1,2-a]pyrimidin-2-yl)-ethylamino]-pyrimidine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-(3-pyridin-2-yl-imidazo[1,2-a]pyrimidin-2-yl)-ethylamine (800 mg, 3.34 mmol) and 4-amino-6-chloro-pyrimidine-5-carbonitrile (520 mg 3.34 mmol) in n-butanol (5 mL) was added DIEA (1.7 mL, 10.04 mmol) at rt. The reaction mixture was stirred at 100° C. overnight. The mixture was concentrated in vacuo. The residue was purified by column chromatography using silica gel (100-200 mesh) and 0-30% acetone in hexane to provide 4-amino-6-[1-(3-pyridin-2-yl-imidazo[1,2-a]pyrimidin-2-yl)-ethylamino]-pyrimidine-5-carbonitrile: 1H NMR: (DMSO-d6, 400 MHz) δ 1.547 (d, J=6.4 Hz, 3H), 5.807-5.841 (br s, 1H), 7.150-7.176 (m, 1H), 7.289 (br s, 2H), 7.429-7.466 (m, 2H), 7.847-7.867 (m, 1H), 7.998 (s, 2H), 8.653 (s, 1H), 8.789 (s, 1H), 9.419 (d, J=6.4 Hz, 1H); LC-MS (ESI) m/z 358.2 [M+H]+.

Provenance & Evidence