Methyl iodide → 7-Benzyl-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4(4aH)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of ethyl N-benzyl-3-oxo-4-piperidine-carboxylate hydrochloride (8.9 g, 30 mmol) and thiourea (4.56 g, 60 mmol) in a solution of sodium methoxide in methanol (34 mL, 25% wt/wt) was stirred at 100° C. in a sealed tube overnight. Iodomethane (5.1 g, 42 mmol) was added dropwise to the reaction mixture after cooling to room temperature and stirred at room temperature for 1 hr. Solvent was removed in vacuo and the residue was dissolved in water (100 mL), extracted by CHCl3 and i-PrOH (3:1, 10×40 mL) and dried over sodium sulfate. Solvent was removed in vacuo, product was obtained as a beige powder (7.6 g).

Provenance & Evidence