Cesium carbonate → HCID 59606006, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(5-chloro-7-morpholin-4-yl-thiazolo[5,4-d]pyrimidin-2-yl)-1-[4-(1-hydroxy-1-methylethyl)piperidin-1-yl]ethanone (40 mg, 0.09 mmol), 2-ethylbenzimidazole (15 mg, 0.10 mmol), Pd2(dba)3 (2.1 mg, 2.5 mol %), Xphos (4.3 mg, 10 mol %) and Cs2CO3 (44 mg, 0.14 mmol) in dioxane (1.5 mL) was purged with argon gas then heated at 120° C., for 20 h, in a sealed tube. The reaction mixture diluted with EtOAc, filtered through Celite® and evaporated. The resulting residue was purified by column chromatography (Si—PCC, 0-10% MeOH in EtOAc) to give 549 as a pale beige solid (19 mg, 38%). LCMS (Method I): RT=3.47 min, [M+H]+ 550.2. 1H NMR (400 MHz, CHCl3-d): δ 8.02-7.98 (m, 1 H), 7.81-7.76 (m, 1 H), 7.33-7.29 (m, 2 H), 4.81-4.75 (m, 1 H), 4.52-4.29 (m, 4 H), 4.19 (s, 2 H), 4.07 (m, 1 H), 3.89-3.84 (m, 4 H), 3.38 (q, J=7.5 Hz, 2 H), 3.15-3.06 (m, 1 H), 2.63-2.54 (m, 1 H), 1.90-1.92 (m, 2 H), 1.92-1.80 (m, 2 H), 1.61-1.50 (m, 1 H), 1.44 (t, J=7.5 Hz, 3 H), 1.36-1.23 (m, 1 H), 1.20 (d, J=11.0 Hz, 6 H)

Provenance & Evidence