Cesium carbonate → HCID 69669181, compound

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 3-(3-aminopyridin-2-yloxy)azetidine-1-carboxylate (1.56 g, 5.90 mmol) was added into a solution of methyl 4-chloro-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (1.57 g, 6.49 mmol), XANTPHOS (0.683 g, 1.18 mmol) and cesium carbonate (2.69 g, 8.26 mmol) in degassed 1,4-dioxane (50 mL). The mixture was degassed under sonnication, tris(dibenzylideneacetone)dipalladium (0.270 g, 0.30 mmol) added and the mixture sonnicated further. The reaction was sealed, heated at 90° C. overnight and concentrated in vacuo. The product was purified by flash-column chromatography (petroleum ether (40-60° C.) 1:1 petroleum ether (40-60° C.)/EtOAc), trituration from MeCN and reverse phase preparative HPLC to yield the title compound as yellow solid.

Provenance & Evidence