Cesium carbonate → HCID 59605839, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-8-[2-(4-methanesulfonyl-3,3-dimethylpiperazin-1-yl)ethyl]-9-methyl-6-morpholin-4-yl-9H-purine (35 mg, 0.07 mmol), 2-ethylbenzimidazole (12 mg, 0.08 mmol), Pd2(dba)3 (1.7 mg, 2.5 mol %), Xphos (3.5 mg, 10 mol %) and Cs2CO3 (36 mg, 0.11 mmol) in dioxane (1.5 mL) was purged with argon gas then heated at 120° C., for 24 h, in a sealed tube. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3/MeOH in DCM. The resulting residue was purified by reverse phase HPLC (Phenomenex Gemini 5 μm C18, 20 mM triethylamine in water on a gradient of acetonitrile 30-90%) to give 575 (20 mg, 46%) as a pale beige solid. LCMS: (Method I): RT 2.74 min, [M+H]+ 582.2 1H NMR (400 MHz, CDCl3d): δ 8.01-7.96 (m, 1 H), 7.79-7.75 (m, 1 H), 7.28-7.25 (m, 2 H), 4.50-3.96 (m, 4 H), 3.86 (t, J=4.7 Hz, 4 H), 3.78 (s, 3 H), 3.50-3.44 (m, 2 H), 3.36 (q, J=7.4 Hz, 2 H), 3.04 (t, J=7.4 Hz, 2 H), 2.94 (s, 3 H), 2.87 (t, J=7.4 Hz, 2 H), 2.64-2.58 (m, 2 H), 2.38 (s, 2 H), 1.50 (s, 6 H), 1.45 (t, J=7.4 Hz, 3 H)

Provenance & Evidence