2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → HCID 50941330, compound

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Reaction Conditions

Reaction Steps

Compound 2 obtained in step 1 (552 mg, 1.0 mmol) was dissolved in THF (15 ml). To this solution, t-butyllithium (1.76 M in n-pentane, 2.27 mL, 4.0 mmol) was slowly added at −78° C., and this mixture was stirred for 15 minutes. The resulting solution was kept at −40° C. for 30 minutes and then cooled again to −78° C. After 15 minutes passed, this solution was mixed with CuCl (198 mg, 2.0 mmol) and DMPU (0.36 mL, 3.0 mmol), followed by stirring at 0° C. for 0.5 hours. Then, to this reaction mixture, 2,3-diiodonaphthalene (760 mg, 2.0 mmol) was added and heated at 50° C. for 12 hours. The reaction mixture was cooled to 0° C. and then quenched with 3 N HCl, and the reaction product was extracted with hexane. The organic layer was washed with saturated aqueous sodium bicarbonate and aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate:triethylamine=50:1:1) to give the titled compound (compound 3) as a yellow solid (169 mg, yield: 40%).

Provenance & Evidence