Triethylamine → HCID 136121491, compound

Participants

Reaction Steps

To a solution of 2-(4-chloro-7-methylquinazolin-2-yl)phenol (0.5 g, 1.84 mmol) in CH2Cl2 (10 mL) at 0° C. was added dropwise a solution of tert-butyl (R)-piperidin-3-ylcarbamate (0.37 g, 1.84 mmol) in CH2Cl2 (5 mL), then triethylamine (0.51 μL, 3.68 mmol). The mixture was allowed to warm to room temperature and was stirred for 3 h. After quenching with water, it was extracted with CH2Cl2. The organic layers were combined, dried over MgSO4, and concentrated. Purification via silica gel chromatography using 5:1 CH2Cl2: hexanes gave tert-butyl (R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-ylcarbamate (0.54 g, 68%). LC/MS: m/z 435.5 (M+H)+ at 2.80 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Provenance & Evidence