Cesium carbonate → {1-[4-Methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-pyrrolidin-2-ylmethyl}-carbamic acid tert-butyl ester

Participants

Reaction Steps

A mixture of 6-bromo-4-methyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Preparation #1, Step E, 0.050 g, 0.117 mmol), cesium carbonate (0.076 g, 0.235 mmol), tert-butyl (pyrrolidin-2-ylmethyl)carbamate (0.047 g, 0.235 mmol), Pd(OAc)2 (0.008 g, 0.035 mmol) and BINAP (0.022 g, 0.035 mmol) in toluene (2 mL) was heated at reflux overnight. The reaction mixture was cooled to ambient temperature, filtered and concentrated in vacuo to give crude tert-butyl ((1-(1-methyl-2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)pyrrolidin-2-yl)methyl)carbamate as brown solid, which was used for next step without further purification.

Provenance & Evidence