Cesium carbonate → HCID 59605954, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (44 mg, 0.10 mmol), 2-ethylbenzimidazole (17 mg, 0.11 mmol), Pd2(dba)3 (2.4 mg, 2.5 mol %), Xphos (5.0 mg, 10 mol %) and Cs2CO3 (51 mg, 0.16 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 was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3/MeOH in DCM. The resulting residue was purified by column chromatography (Si—PCC, 0-100% EtOAc in cyclohexane) to give 646 (37 mg, 67%) as a yellow solid. LCMS: (Method I): RT 4.34 min, [M+H]+ 533.2 1H NMR (400 MHz, CDCl3d): δ 8.01-7.97 (m, 1 H), 7.78-7.73 (m, 1 H), 7.29-7.22 (m, 2 H), 4.55-4.10 (m, 4 H), 3.86 (t, J=4.67 Hz, 4 H), 3.80 (s, 3 H), 3.80-3.44 (m, 4 H), 3.35 (q, J=7.48 Hz, 2 H), 2.36 (s, 3 H), 1.49 (s, 9 H), 1.44 (t, J=7.48 Hz, 3 H)

Provenance & Evidence