Cesium carbonate → HCID 59605506, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[2-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)ethyl]-3-methylazetidin-3-ol (80 mg, 0.22 mmol), 2-ethylbenzimidazole (35 mg, 0.24 mmol), Pd2(dba)3 (5 mg, 2.5 mol %), Xphos (10.4 mg, 10 mol %) and Cs2CO3 (107 mg, 0.33 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 in MeOH. The resulting residue was purified by flash chromatography (Si—PCC, 0-10% 2 M NH3/MeOH in DCM) to give 458 (77 mg, 74%) as a pale beige solid. LCMS: (Method I): RT 2.39 min; [M+H]+ 477.2. 1H NMR (400 MHz, CHCl3-d): δ 8.01-7.96 (m, 1 H), 7.76-7.72 (m, 1 H), 7.26-7.22 (m, 2 H), 4.45-4.32 (m, 4 H), 3.86 (t, J=4.8 Hz, 4 H), 3.77 (s, 3 H), 3.40 (d, J=7.3 Hz, 2 H), 3.34 (q, J=7.5 Hz, 2 H), 3.14 (d, J=7.3 Hz, 2 H), 3.02 (t, J=7.3 Hz, 3 H), 2.92 (t, J=7.3 Hz, 2 H), 1.53 (s, 3 H), 1.44 (t, J=7.5 Hz, 3 H)

Provenance & Evidence