Diisopropylethylamine → HCID 67431833, compound

Participants

Reaction Conditions

Reaction Steps

To the crude (S)-methyl 2-(1-aminoethyl)-3-phenylimidazo[1,2-a]pyridine-5-carboxylate (500 mg, 1.69 mmol) and 4-amino-6-chloro-pyrimidine-5-carbonitrile (268 mg, 1.69 mmol) in n-butanol (5 mL) was added DIEA (0.5 mL, 2.54 mmol) at 25° C. The reaction mixture was stirred at 110° C. for 5-6 h. The mixture was extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography using silica gel (100-200 mesh) and 0-40% acetone in hexane to provide (S)-methyl 2-[1-((6-Amino-5-cyanopyrimidin-4-yl)amino)ethyl]-3-phenylimidazo-[1,2-a]pyridine-5-carboxylate: 1H NMR (400 MHz, DMSO-d6) δ 1.471 (d, J=6.8 Hz, 3H), 3.111 (s, 3H), 5.352-5.420 (m, 1H), 6.935-6.954 (m, 1H), 7.259-7.518 (m, 9H), 7.882-7.941 (m, 2H); LC-MS (ESI) m/z 414.1 [M+H]+.

Provenance & Evidence