1-Hydroxybenzotriazole → N-(2-aminoethyl)-3-(6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzamide

Participants

Reaction Steps

To a solution of 3-(6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid obtained from step 2 of Example 57 (16.9 mg, 48 μmol) and tert-butyl 2-aminoethylcarbamate (6.4 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, taken up in methanol (1 mL) and 4.0 N hydrochloric acid in dioxane (1 mL), and stirred at room temperature for 4 hours then concentrated. 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-aminoethyl)-3-(6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzamide (3.4 mg, 23%).

Provenance & Evidence