Dimethyl Sulfoxide → 2-((1S)-1-((6-amino-5-(methylsulfonyl)-4-pyrimidinyl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of copper(II) triflate (7.6 mg, 0.021 mmol), sodium methanesulfinate (25.7 mg, 0.251 mmol), (S)-2-(1-(6-amino-5-iodopyrimidin-4-ylamino)ethyl)-1-cyclopropyl-N-methyl-1H-benzo[d]imidazole-7-carboxamide (prepared in Example 21, 100 mg, 0.210 mmol) under N2, N,N′-dimethylethylenediamine (4.52 μL, 0.042 mmol) and DMSO (1 mL) were added. The mixture was placed in a 110° C. oil bath. After stirring for 18 h at 110° C., the mixture was cooled to rt, diluted with EtOAc, and filtered through a pad of silica gel. The filtrate was washed with water, brine, dried and concentrated under reduced pressure. The residue was purified by column chromatography on a silica gel column using 0 to 10% gradient of MeOH in DCM-EtOAc (1:1) 0.2% NH4OH as eluent to give 2-((1S)-1-((6-amino-5-(methylsulfonyl)-4-pyrimidinyl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide: 1H NMR (400 MHz, CDCl3) 8.02-7.97 (m, 2H), 7.65 (d, J=8 Hz, 1H), 7.22 (d, J=8 Hz, 1H), 7.12 (dd, J=8, 8 Hz, 1H), 6.01-5.92 (m, 2H), 3.45-3.40 (m, 2H), 3.16 (s, 3H), 3.01 (d, J=4 Hz, 3H), 1.61 (d, J=4 Hz, 3H), 1.22-1.10 (m, 2H), 1.04-0.96 (m, 1H), 0.80-0.73 (m, 1H); LC-MS (ESI) m/z 430.1 [M+H]+.

Provenance & Evidence