Cesium carbonate → 5-(2-Ethylbenzoimidazol-1-yl)-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carbaldehyde (1.0 g, 3.51 mmol), 2-ethylbenzimidazole (512 mg, 3.71 mmol), tris(dibenzylideneacetone)dipalladium (90 mg, 2.5 mol %), XPhos (158 mg, 10 mol %) and Cs2CO3 (1.6 g, 4.91 mmol) in dioxane (30 mL) was purged with argon then heated at 115° C. for 17 h. The reaction mixture was filtered through Celite® which was washed with hot dioxane, and the filtrated concentrated in vacuo. The resulting residue was triturated with Et2O and the resulting brown solid collected by filtration and dried in vacuo affording the title compound (1.23 g, 88%). 1H NMR (CDCl3, 400 MHz): δ 10.01 (1 H, s), 8.09-8.09 (1 H, m), 7.75-7.74 (1 H, m), 7.33-7.26 (2 H, m), 5.00-4.00 (4 H, brd s), 3.93 (4 H, t, J=4.72 Hz), 3.37 (2 H, q, J=7.45 Hz), 1.46 (3 H, t, J=7.45 Hz).

Provenance & Evidence