Lithium Chloride → HCID 86723421, compound

Participants

Reaction Steps

4-Methyl-2-tributylstannanyl-thiazole (Intermediate J) (491 mg, 1.265 mmol) was added to a suspension of trifluoro-methanesulfonic acid 2,4-dimethyl-1,3-dioxo-9-phenyl-1,2,3,4,7,8-hexahydro-2,4,8a-triaza-fluoren-5-yl ester (Intermediate K) (480 mg, 1.054 mmol), lithium chloride (4.47 mg, 0.105 mmol), copper(I) iodide (20.07 mg, 0.105 mmol) and PdCl2(dppf) (77 mg, 0.105 mmol) in THF (12 ml) and the mixture heated at reflux under nitrogen for 2 h. Further 4-methyl-2-tributylstannanyl-thiazole (Intermediate J) (491 mg, 1.265 mmol) was added and the mixture continued at reflux for 2 h, then further 4-methyl-2-tributylstannanyl-thiazole (Intermediate J) (491 mg, 1.265 mmol) was added and the mixture stirred at reflux for 1 h. The mixture was cooled to RT, diluted with EtOAc and washed with dilute aqueous NH4OH, water and brine. The organic phase was dried over sodium sulphate and evaporated under reduced pressure. The residue was triturated with MeOH/Et2O and the precipitate collected by filtration. The precipitate was purified by chromatography on silica, eluting with 50% EtOAc in hexane. Trituration with Et2O and collection by filtration afforded 1,3-dimethyl-10-(4-methylthiazol-2-yl)-5-phenyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione as a pale yellow solid

Provenance & Evidence