Benzoyl chloride → 1-[6-benzoylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

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Reaction Steps

Benzoyl chloride (81.1 μL, 0.698 mmol) was added dropwise to a solution of 1-[6-amino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.200 g, 0.466 mmol), TEA (0.162 mL, 1.16 mmol), and DCM (2.3 mL). The reaction mixture was stirred at room temperature for 1.5 h and was then diluted with DCM (25 mL) and quenched with water (15 mL). The organic layer was washed with water (20 mL) and brine (20 mL), dried (MgSO4), and concentrated. The residue was purified by FCC (10-70% EtOAc/hexanes) to yield the titled compound (0.240 g, 97% yield). MS (ESI/Cl): mass calcd. for C27H31N5O5Si, 533.2; m/z found, 476.2 [M+H−58]+.

Provenance & Evidence