Triethylamine → HCID 136350273, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromoquinazolin-4(3H)-one (0.50 g, 2.22 mmol), 1,4-diazabicyclo[3.2.2]nonane hydrochloride (0.44 g, 2.22 mmol), triethylamine (0.45 g, 4.44 mmol), potassium tert-butoxide (0.25 g, 2.22 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (1.06 g, 2.22 mmol) and tris(dibenzyllideneacetone)dipalladium (0) (0.41 g, 0.44 mmol) in Tetrahydrofuran (15 mL) was heated in the microwave at 120° C. for 30 mins. The solvent was evaporated off and to the residue was added methanol and the mixture acidified with acetic acid then loaded on to a 5 g SCX column. The mixture was purified on silica (25 g SNAP column on SP4) eluting with dichloromethane to 60/40 dichloromethane/(2M ammonia in methanol) to afford 6-(1,4-diazabicyclo[3.2.2]nonan-4-yl)quinazolin-4(3H)-one (18.5 mg, 0.07 mmol).

Provenance & Evidence