N-Methyl dicyclohexylamine → HCID 86723420, compound

Participants

Reaction Conditions

Reaction Steps

1,3-dimethyl-5-phenyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (Intermediate I), 2-bromo-5-methylfuran (commercially available) (390 mg, 2.421 mmol), palladium acetate (commercially available) (36.2 mg, 0.161 mmol), tri-tert-butylphosphine tetrafluorohydroborate (commercially available) (94 mg, 0.323 mmol) and N-cyclohexyl-N-methylcyclohexylamine (commercially available) (0.691 mL, 3.23 mmol) were combined in dimethyl acetamide (4 mL) and the mixture sparged with nitrogen for 30 min. The mixture was then heated at 120° C. for 15 h under microwave irradiation. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic phases were washed with brine, dried over sodium sulphate and evaporated under reduced pressure. Purification by chromatography on silica, eluting with 20% EtOAc in iso-hexane, afforded 1,3-dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione as a yellow solid which was used without further purification.

Provenance & Evidence