Cesium carbonate → HCID 59605310, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [2-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)ethyl]methyl-(3-methyl-1,1-dioxotetrahydrothiophen-3-yl)amine (87 mg, 0.20 mmol), 2-ethylbenzimidazole (32 mg, 0.22 mmol), tris(dibenzylideneacetone)dipalladium (5 mg, 2.5 mol %), XPhos (9 mg, 10 mol %) and Cs2CO3 (96 mg, 0.30 mmol) in dioxane (2 mL) was purged with argon then heated at 110° C. for 20 h in a sealed tube. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH/DCM. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-5%) affording 748 as an off-white solid (60 mg, 55%). LCMS (method I): RT 2.63 min, [M+H]+ 553.1. 1H NMR (CDCl3, 400 MHz): δ 8.01-7.98 (1 H, m), 7.75-7.74 (1 H, m), 7.30-7.23 (2 H, m), 4.34 (4 H, brd s), 3.87 (4 H, t, J=4.78 Hz), 3.78 (3 H, s), 3.37-3.30 (3 H, m), 3.01-3.00 (7 H, m), 2.40-2.30 (4 H, m), 2.08-2.08 (1 H, m), 1.44 (3 H, t, J=7.48 Hz), 1.29 (3 H, s)

Provenance & Evidence