Sulfuric Acid → HCID 59128641, compound

Participants

Reaction Conditions

Reaction Steps

Propane-2-one oxime (62 mg, 0.844 mmol) was dissolved in 2 mL THF and cooled to 0° C. under nitrogen. n-Butyl lithium (0.68 mL of 2.5 M solution in hexanes, 1.688 mmol) was added slowly, so that the reaction temperature remained below 5° C. After stirring for 30 minutes, 4-methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzoic acid methyl ester (200 mg, 0.56 mmol) was added, and the reaction mixture was stirred at 0° C. for one hour. Concentrated sulfuric acid (0.43 mL) was added dropwise, and the temperature was allowed to warm to room temperature over one hour. The reaction mixture was made pH neutral by addition of 1 M aqueous NaOH, and then partitioned between water and methylene chloride. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by preparative scale TLC plate, eluting with 25% EtOAc in hexanes then again with 0.25% MeOH in CH2Cl2, to give 8 mg of 8-methyl-6-[2-methyl-5-(3-methyl-isoxazol-5-yl)-phenyl]-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one; MS (M+H)=379.

Provenance & Evidence