Cesium carbonate → HCID 68157107, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-amino-6-[(S)-1-(7-bromo-1-methyl-1H-benzoimidazol-2-yl)ethylamino]pyrimidine-5-carbonitrile (100 mg, 0.27 mmol), 4-cyanobenzeneboronic acid (51 mg, 0.35 mmol), Pd(PPh3)4 (31 mg, 0.03 mmol) and Cs2CO3 (175 mg, 0.54 mmol) in dioxane (3 mL) and H2O (1.5 mL) was heated for 30 min by microwave irradiation at 140° C. The reaction solution was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH, followed by 2M NH3 in MeOH. The basic fractions were combined and concentrated in vacuo. The resulting residue was dissolved in DCM and the fine precipitate filtered and washed with DCM. The filtrate was concentrated in vacuo and purified by column chromatography (Si—PPC, gradient 0-10% 2M NH3 in MeOH/DCM) to afford 423 as a white solid (36 mg, 34%). LCMS (Method K): RT 2.30 min [M+H]+ 395. 1H NMR (DMSO-d6, 400 MHz): δ 8.04 (1H, s), 7.96-7.94 (2H, m), 7.72-7.67 (4H, m), 7.32 (2H, bs), 7.27, (1H, dd, J=8.0, 7.5 Hz), 7.07 (1H, dd, J=7.5, 1.0 Hz), 5.66 (1H, dq, J=7.0, 7.0 Hz), 3.28 (3H, s), 1.60 (3H, d, J=7.0 Hz)

Provenance & Evidence