Ethanol → N-(4-{[3-(6-Amino-4-hydroxy-2-imino-1,2-dihydropyrimidin-5-yl)propyl]amino}benzoyl)glutamic acid

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Reaction Steps

A stirred solution of 1.60 g (2.89 mmol) of dimethyl N-[4-[3-(2,4-bis(acetamido)-1,6-dihydro-6-oxo-5-pyrimidinyl)propylamino]benzoyl]-L-glutamate, 50 ml of ethanol and 100 ml of 1 N sodium hydroxide was heated at 50°-60° for 20 hours. The cooled reaction was spin evaporated in vacuo to 50 ml, cooled, and neutralized to pH 5-6 with concentrated hydrochloric acid. The resultant white precipitate was collected, washed with water, diethylether and dried; yield, 0.86 g (66%) mp (sinter 170°) 198°-202° (eff). Recrystallization from methanol gave the analytical sample; yield, 0.33 g (39%), mp (forms hard foam 180°) 200° (eff); TLC (pyridine:BuOH:H2O/1:1:1); NMR (DMSO-D6)δ8.07 (d, 1H, ArCONH), 7.65 (d, 2H, ArH), 6.54 (d, 2H, ArH), 6.22 (br s, 1H, CH2NH), 5.94 (s, 2H, NH2), 5.75 (s, 2H, NH2), 4.34 (m, 1H, CHCO2H), 3.03 (m, 2H, CH2NHAr), 2.30 (m, 4H, pyrimidine-CH2 and CH2CO2H), 2.03 (m, 2H, CHCH2), 1.58 (m, 2H, CH2CH2CH2).

Provenance & Evidence