Cesium carbonate → HCID 59606084, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[2-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)ethyl]-6-isopropylpiperazin-2-one (90 mg, 0.21 mmol), 2-ethylbenzimidazole (35 mg, 0.24 mmol), Pd2(dba)3 (4.9 mg, 2.5 mol %), Xphos (10.2 mg, 10 mol %) and Cs2CO3 (104 mg, 0.32 mmol) in dioxane (2.0 mL) was purged with argon gas then heated at 120° C., for 19 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 20-90%) to give 522 (50 mg, 44%) as a pale beige solid. LCMS: (Method I): RT 2.90 min; [M+H]+ 532.3. 1H NMR (400 MHz, CHCl3-d): δ 8.01-7.96 (m, 1 H), 7.84-7.78 (m, 1 H), 7.32-7.28 (m, 2 H), 5.82 (s, 1 H), 4.62-4.07 (m, 4 H), 3.86 (t, J=4.7 Hz, 4 H), 3.78 (s, 3 H), 3.47-3.23 (m, 4 H), 3.08-2.99 (m, 4 H), 3.01-2.93 (m, 2 H), 2.40 (dd, J=11.7, 8.9 Hz, 1 H), 1.79-1.67 (m, 1 H), 1.47 (t, J=7.5 Hz, 3 H), 0.98 (d, J=6.8 Hz, 3 H), 0.95 (d, J=6.88 Hz, 3 H)

Provenance & Evidence