Triethylamine → HCID 11948303, compound

Participants

Reaction Steps

To a solution of 1-(4-aminobenzyl)-3-(4-tert-butylbenzyl)-tetrahydropyrimidin-2-one (L) (438 mg, 1.24 mmol) and triethylamine (0.22 mL, 1.6 mmol) in abs. THF (50 mL) there was added a solution of methanesulphonyl chloride (0.11 mL, 1.48 mmol) in 5 mL of abs. THF within a period of 15 min. The reaction mixture was stirred over a period of 48 h at RT, sat. NaHCO3 solution (20 mL) was added, and the mixture was stirred for 30 min. H2O (30 mL) was added, and the mixture was extracted with EtOAc (3×30 mL). The combined organic phases were washed with sat. NaCl solution (30 mL), dried over Na2SO4, and the solvent was removed in vacuo. The residue was purified by means of column chromatography (SiO2 (50 g) using cyclohexane/EtOAc 1:1 (500 mL) as eluent). The desired product N-{4-[3-(4-tert-butyl benzyl)-2-oxotetrahydropyrimidin-1-yl methyl]phenyl}methanesulfonamide (5) was obtained as a white solid (398 mg, 75% of theory) having a melting point of 132-135° C.

Provenance & Evidence