Cesium carbonate → HCID 59605327, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-{4-[2-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)ethyl]piperazin-1-yl}isobutyramide (80 mg, 0.18 mmol), 2-methylbenzimidazole (26 mg, 0.20 mmol), Pd2(dba)3 (4 mg, 2.5 mol %), Xphos (8 mg, 10 mol %) and Cs2CO3 (87 mg, 0.27 mmol) in dioxane (1.0 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% MeOH in DCM) to give 368 (63 mg, 65%) as a pale yellow solid. LCMS: (Method G): RT 5.34 min; [M+H]+ 547.3. 1H NMR (400 MHz, CHCl3-d): δ 8.09-8.05 (m, 1 H), 7.73-7.69 (m, 1 H), 7.29-7.24 (m, 1 H), 7.06 (s, 1 H), 5.23 (s, 1 H), 4.47-4.14 (m, 4 H), 3.87 (t, J=4.7 Hz, 4 H), 3.79 (s, 3 H), 3.49 (s, 1 H), 3.19-3.0 (m, 2 H), 2.94 (s, 3 H), 2.78-2.54 (m, 6 H), 1.78-1.48 (m, 4 H), 1.25 (s, 6 H)

Provenance & Evidence