Cesium carbonate → HCID 59605899, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-8-[2-(2,2-dimethylmorpholin-4-yl)ethyl]-9-methyl-6-morpholin-4-yl-9H-purine (57 mg, 0.14 mmol), 2-ethylbenzimidazole (23 mg, 0.16 mmol), Pd2(dba)3 (3.3 mg, 2.5 mol %), Xphos (6.9 mg, 10 mol %) and Cs2CO3 (71 mg, 0.27 mmol) in dioxane (1.0 mL) was purged with argon gas then heated at 120° C., for 16 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, 0-5% MeOH in DCM) to give 392 (46 mg, 63%) as a pale yellow solid. LCMS: (Method G): RT 6.31 min; [M+H]+ 505.3. 1H NMR (400 MHz, CHCl3-d): δ 8.02-7.97 (m, 1 H), 7.78-7.72 (m, 1 H), 7.27-7.22 (m, 2 H), 4.48-4.20 (m, 4 H), 3.89-3.83 (m, 4 H), 3.79 (s, 3 H), 3.77-3.55 (m, 2 H), 3.35 (q, J=7.5 Hz, 2 H), 3.12-2.97 (m, 2 H), 2.91-2.76 (m, 2 H), 2.57-2.43 (m, 2 H), 2.42-2.29 (m, 2 H), 1.44 (t, J=7.5 Hz, 3 H), 1.26 (s, 6 H)

Provenance & Evidence