Triethylamine → HCID 25214954, compound

Participants

Reaction Steps

To a stirred solution of 3-butene-1-ol (216 mg, 3 mmol) in chloroform (20 mL) cooled in an ice bath under nitrogen atmosphere, was added triethylamine (630 μL, 4.5 mmol) and methanesulfonyl chloride (270 μL, 3.6 mmol) was added dropwise. After stirring for 1.1 hr., the reaction mixture was diluted with dichloromethane and washed with sat. aqueous sodium bicarbonate, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuum for ca. 20 min. and mixed with 3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (Compound 1) (891 mg, 3 mmol), powdered anhydrous potassium carbonate (414 mg, 3.6 mmol), and lithium iodide (402 mg, 3 mmol). DMF (15 mL) was then added to the mixture and stirred for overnight in an oil bath (40-50° C.). After evaporation of DMF, the residue was dissolved in methanol-chloroform (1:9) and filtered through a celite pad. The filtrate was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to afford 320 mg (30%) of 3-(3-but-3-enyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (79) as a white foam. Recrystallization from ether-hexane resulted a white solid. m.p. 133-134° C.; 1H-NMR (300 MHz, CDCl3) δ 1.13 (3H, d, J=6.9 Hz), 1.22 (3H, d, J=6.9 Hz), 2.19-2.34 (3H, m), 2.54 (3H, s), 3.15 (1H, m), 3.90 (1H, m), 4.94-5.02 (2H, m), 5.58 (1H, m), 7.82 (1H, s), 7.96 (1H, s), 8.06 (1H, s), 8.99 (1H, s); m/z (EI) 351 (M+).

Provenance & Evidence