tert-Butyl methylcarbamate → tert-butyl N-methyl-N-[6-(2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)dibenzothiophen-2-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

tert-butyl methylcarbamate (467 mg, 3.56 mmol) dissolved in dioxane (5ml) was added in one portion to 6-(2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (1000 mg, 1.78 mmol) , TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (40.8 mg, 0.04 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (51.5 mg, 0.09 mmol) and cesium carbonate (2321 mg, 7.12 mmol) in degassed dioxane (18 mL), under nitrogen, at 110 °C. The reaction flask was evacuated and blanketed with nitrogen 4X. The resulting suspension was stirred at 110 °C for 3 __ hours with complete reaction observed by LCMS. After cooling, the mixture was partitioned between EtOAc (100mL) and water (50ml). The organics were separated and dried (MgSO4) and evaporated to give the crude product, tert- butyl methyl(6-(2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)dibenzo[b,d]thiophen-2-yl)carbamate (950 mg, 98 %) which was combined with the crude product from EN02472-66 and purified (proceedure detailed on that page). m/z (ES+) (M+H)+ = 543; HPLC tR= 2.91 min.

Provenance & Evidence