Cesium carbonate → HCID 67492197, compound

Participants

Reaction Steps

A mixture of 2-chloro-8-((1S,4S)-5-methanesulfonyl-2,5-diazabicyclo[2.2.1]hept-2-ylmethyl)-9-methyl-6-morpholin-4-yl-9H-purine (150 mg, 0.34 mmol), 2-ethyl-1H-benzoimidazole (59 mg, 0.40 mmol), Pd2dba3 (9 mg, 0.009 mmol), Xphos (18 mg, 0.036 mmol) and cesium carbonate (165 mg, 0.51 mmol) in 1,4-dioxane (3 mL) was purged with argon gas then subjected to microwave irradiation at 150° C. for 30 min. 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, EtOAc:MeOH 100:0 to 99:1 to 98:2) to afford 553 as a white solid (153 mg, 82%). LCMS (Method I): RT=2.53 min, M+H+=552. 1H NMR (CDC3, 400 MHz) δ 8.01 (m, 1 H); 7.77 (m, 1 H); 7.28 (m, 2 H); 4.35 (m, 5 H); 4.06 (d, J=13.6 Hz, 1 H); 3.96 (d, J=13.6 Hz, 1 H); 3.87 (m, 7 H); 3.65 (d, J=9.5 Hz, 1 H); 3.61 (bs, 1 H); 3.37 (q, J=7.5 Hz, 2 H); 3.27 (dd, J=9.5, 2.3 Hz, 1 H); 3.02-2.93 (m, 2 H); 2.91 (s, 3 H); 1.99 (d, J=10.2 Hz, 1 H); 1.79 (d, J=10.2 Hz, 1 H) and 1.45 (t, J=7.5 Hz, 3 H)

Provenance & Evidence