Cesium carbonate → HCID 59605654, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-{1-[2-(5-chloro-7-morpholin-4-yl-thiazolo[5,4-d]pyrimidin-2-yl)ethyl]-piperidin-4-yl}propan-2-ol (56 mg, 0.13 mmol), 2-ethylbenzimidazole (21 mg, 0.15 mmol), Pd2(dba)3 (3.0 mg, 2.5 mol %), Xphos (6.3 mg, 10 mol %) and Cs2CO3 (64 mg, 0.20 mmol) in dioxane (1.0 mL) was purged with argon gas then heated at 120° C., for 18 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 433 (39 mg, 56%) as an orange solid. LCMS: (Method I): RT 2.71 min; [M+H]+ 536.4. 1H NMR (400 MHz, CHCl3-d): δ 8.01-7.97 (m, 1 H), 7.76-7.71 (m, 1 H), 7.29-7.24 (m, 2 H), 4.52-4.32 (m, 4H), 3.90-3.85 (m, 4 H), 3.34 (q, 7.5 Hz, 2 H), 3.35-3.23 (m, 2 H), 3.21-3.10 (m, 2 H), 2.87-2.83 (m, 2 H), 2.17-2.05 (m, 2 H), 1.86-1.75 (m, 2 H), 1.43 (t, J=7.5 Hz, 3 H), 1.38-1.23 (m, 3 H), 1.22 (s, 6 H)

Provenance & Evidence