Triethylamine → (R)-1-(4-(6-bromo-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one

Participants

Reaction Steps

To a solution of 2-(6-bromo-4-chloroquinazolin-2-yl)phenol (228 mg, 0.68 mmol), triethylamine (129 μL, 0.92 mmol), and CH2Cl2 (6 mL) was added (R)-2-hydroxy-4-methyl-1-(piperazin-1-yl)pentan-1-one (185 mg, 0.92 mmol) dissolved in CH2Cl2 (3 mL). The flask was flushed with N2 and stirred for 3 hours. The reaction mixture was then transferred into a separatory funnel with CH2Cl2, and the organic phase was washed with H2O (2×), dried over Na2SO4, and concentrated. Purification via silica gel chromatography using 0 to 20% EtOAc and CH2Cl2:hexanes (1:1) gave (R)-1-(4-(6-bromo-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one (285 mg, 84%). LC/MS: m/z 500.30 (M+H)+ at 3.29 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Provenance & Evidence