Bromobenzene → Ammonium Hydroxide

Participants

Reaction Conditions

Reaction Steps

5,6,7,8-Tetrahydro-imidazo[1,2-a]pyrazine, prepared as described in PCT Application WO 01/44250, was coupled with 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b, as described herein. 2-(5,6-dihydro-8H-imidazo[1,2-a]pyrazin-7-yl)-6,7-dimethoxy-1H-quinazolin-4-one (150 mg, 0.46 mmol) was combined with bromobezene (97 μL, 0.92 mmol), potassium carbonate (127 mg, 0.92 mmol), palladium acetate (5 mg, 5 mol %), and triphenylphosphine (13 mg, 10 mol %) in DMF (6 mL). The mixture was heated in a 140° C. bath for 2 d, then concentrated onto silica gel followed by eluting with 300:10:1 CH2Cl2:MeOH:NH4OH) to afford 50 mg of 6,7-dimethoxy-2-(3-phenyl-5,6-dihydro-8H-imidazo[1,2-α]pyrazin-7-yl)-1H-quinazolin-4-one, 904, mp: >300° C, M+=403.

Provenance & Evidence