2-Ethylaminoethyldimethylamine → N-[2-(dimethylamino)ethyl]-N-ethyl-4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]benzamid

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Reaction Steps

To a solution of 4-(6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid (16.9 mg, 48 μmol) and N,N-dimethyl-N′-ethylethylenediamine (4.6 mg, 40 μmol) in dichloroethane (1.25 mL) and N,N-dimethylformamide (0.79 mL) was added 1-hydroxybenzotriazole (6.8 mg, 50 μmol) followed by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide (17.8 mg, 60 μmol). The resultant mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated in vacuo. Purification of the residue by HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) followed by concentration in vacuo gave the title compound N-[2-(dimethylamino)ethyl]-N-ethyl-4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]benzamid (3 mg, 20%). 1H NMR (400 MHz, d6-DMSO): 8.21 (m, 3H), 7.97 (s, 1H), 7.87 (dd, 1H), 7.49 (m, 3H), 6.90 (d, 1H), 3.41 (m, 4H), 2.33 (m, 2H), 2.22 (m, 6H), 1.97 (s, 3H), 1.10 (m, 3H); MS (EI) for C24H28N4O3: 421 (MH+).

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