Water → (+/-)-[3-[bis(phenylmethyl)amino]-2-hydroxypropyl]-2(1H)pyrimidinone

Participants

Reaction Conditions

Reaction Steps

A solution of 2-hydroxypyrimidine (0.16 mol) in methanol (300 ml) was stirred at room temperature for 30 minutes. A solution of Na2CO3 (0.16 mol) in methanol (40 ml) was added. The mixture was stirred and refluxed for 15 minutes and cooled to 55° C. A solution of N,N-bis(phenylmethyl)-2-oxiranemethanamine (0.16 mol) in toluene (320 ml) was added dropwise. The mixture was stirred at 50° C. overnight. Water (150 ml) was added. The mixture was stirred at 55° C. for 15 minutes. The organic layer was separated, washed with water, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97/3). The pure fractions were collected and the solvent was evaporated, yielding 26.55 g of (±)-1-[3-[bis(phenylmethyl)amino]-2-hydroxypropyl]-2(1H)pyrimidinone (intermediate 4).

Provenance & Evidence