Water → HCID 10422576, compound

Participants

Reaction Steps

2,4,5-Triamino-6-benzyloxypyrimidine (Pfleiderer et al., Chem. Ber., 94, 12-18 (1961)) (1.85 g, 8 mmol) and 1,1′-carbonyldiimidazole (1.30 g, 8 mmol) were dissolved in anhydrous N,N-dimethylformamide (5 mL) under argon. The solution was stirred at room temperature overnight and was mixed with water (200 mL) to precipitate a white solid. The solid was collected by filtration, and dissolved in 250 mL of aqueous 2 N NaOH solution. Undissolved material was removed by filtration, and the filtrate was neutralized with glacial acetic acid to precipitate a white solid. The solid was collected by filtration, was washed with water, and was recrystallized from 50% aqueous ethanol to afford analytically pure 1c: yield, 1.63 g (79%); mp 256-257° C. dec.; UV (pH 1) λmax 243 nm (ε=0.717×104), 306 (1.499×104); (pH 6.9) 243 (0.915×104), 290 (1.108×104); (pH 13) 249 (sh) (0.443×104), 293 (1.368×104); 1H NMR δ 5.41 (s, 2H, ArCH2), 6.13 (s, 2H, NH2, exchange with D2O), 7.33-7.51 (m, 5H, ArH), 10.46 (s, 1H, exchanges with D2O), 11.04 (s, 1H, exchanges with D2O); MS (EI) Calcd. m/z for C12H11N5O2: 257.0912. Found: 257.0914. Anal. (C12H11N5O2. 1/2 H2O) C, N, H.

Provenance & Evidence