Cesium carbonate → HCID 67492228, compound

Participants

Reaction Steps

A mixture of 2-[(1S,4S)-5-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]-2-methylpropan-1-ol (50 mg, 0.12 mmol), 2-ethyl-1H-benzoimidazole (20 mg, 0.14 mmol), Pd2dba3 (3 mg, 0.003 mmol), Xphos (6 mg, 0.012 mmol) and cesium carbonate (56 mg, 0.17 mmol) in DMF (1 mL) was purged with argon gas then subjected to microwave irradiation at 150° C. for 1 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge (10 g), which was washed with MeOH/DCM before the desired product was eluted with 2 M NH3 in MeOH/DCM. The product was collected and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PPC, DCM:MeOH 100:0 to 95:5 to 90:10 to 80:20) to afford 521 as a tan solid (27 mg, 44%). LCMS (Method I): RT=2.50 min, M+H+=546. 1H NMR (CDCl3, 400 MHz) δ 8.01 (m, 1 H); 7.75 (m, 1 H); 7.28 (m, 2 H); 4.34 (m, 4 H); 4.02 (m, 2 H); 3.93-3.79 (m, 7 H); 3.49 (m, 2 H); 3.45-3.27 (m, 3 H); 2.89 (m, 2 H); 1.85 (s, 2 H); 1.64 (m, 3 H); 1.48-1.42 (m, 3 H) and 1.33-1.08 (m, 6 H)

Provenance & Evidence