Triethylamine → N-{4-[6-(3,5-Dimethyl-benzoyl)-5-isopropyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl]-pyridin-2-yl}-acetamide

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Reaction Steps

N-(4-Hydroxymethyl-pyridin-2-yl)-acetamide (166 mg, 1 mmol) was dissolved in chloroform (10 ml) and cooled in an ice bath under nitrogen atmosphere. With stirring, triethylamine (210 μl, 1.5 mmol) was added and methanesulfonyl chloride (90 μl, 1.2 mmol) was added dropwise. After stirring for 1.1 hr., the reaction mixture was washed with saturated aqueous sodium bicarbonate, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo for ca. 20 min. and mixed with (20) (286 mg, 1 mmol), powdered anhydrous potassium carbonate (138 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol). DMF (5 ml) was then added to the mixture at room temperature and stirred for ca. 4 hr. After evaporation of DMF, the residue was dissolved in methanol-chloroform (1:9) and filtered through celite pad. The filtrate was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (2:1)) to afford 165 mg (38%) a white solid. m.p. 244-245° C.; 1H NMR (200 MHz, CDCl3) δ 1.17 (3H, d, J=6.7 Hz), 1.24 (3H, d, J=6.7 Hz), 2.20-2.40 (10H, m), 4.70 (1H, d, J=17.1 Hz), 4.88 (1H, d, J=17.1 Hz), 6.82 (1H, d, J=5.3 Hz), 7.24 (1H, s), 7.42 (2H, s), 7.99 (1H, s), 8.30 (1H, d, J=5.3 Hz), 10.01 (1H, s), 12.44 (1H, s); m/z (EI) 434 (M+).

Provenance & Evidence