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Stage #1: With Iodine monochloride In methanol at 25℃; for 15 h; Stage #2: With sodium hydroxide In water at 25℃; for 2 h;
To a flame-dried 100 mL round-bottom flask was added 2,4-diaminopyrimidine (1.0 g, 9.08 mmol) in MeOH (30 mL) followed by dropwise addition of ICl (30 mL, 29.06 mmol). The solution was stirred at 25° C. for 15 h and then the solvent removed under reduced pressure. The resulting viscous oil was stirred in Et2O (40 mL) for 45 min. The resulting solid was filtered off and washed with Et2O (3.x.10 mL) to afford the HCl salt as a yellow solid (3.14 g). The crude salt was suspended in 1.0 N NaOH (100 mL) and stirred at 25° C. for 2 h. The solids were filtered, washed with water (2.x.10 mL), and dried to afford 2,4-Diamino-5-iodopyrimidine as a brown powder (1.71 g, 80percent). An analytical sample was prepared by recrystallization from MeCN to give 2,4-Diamino-5-iodopyrimidine as colorless crystals: Rf=0.25 (9:1, CHCl3:MeOH); mp=212-214° C.; 1H NMR (DMSO-d6) δ 7.92 (s, 1H), 6.40 (s, 2H), 6.10 (s, 2H); 13C NMR (DMSO-d6) δ 162.8, 162.7, 162.0, 61.2; HREI[M+]235.9559 (calculated C4H5IN4: 235.9559); Anal. (C4H5IN4) C, H, N.
Reference：
[1] Nucleosides, Nucleotides and Nucleic Acids, 2009, vol. 28, # 4, p. 275 - 291
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 5, p. 940 - 950
[3] Patent: US2009/105287, 2009, A1, . Location in patent: Page/Page column 26
[4] Chemical Communications, 2015, vol. 51, # 32, p. 7043 - 7046
To a flame-dried 100 mL round-bottom flask was added <strong>[156-81-0]2,4-diaminopyrimidine</strong> (1.0 g, 9.08 mmol) in MeOH (30 mL) followed by dropwise addition of ICl (30 mL, 29.06 mmol). The solution was stirred at 25 C. for 15 h and then the solvent removed under reduced pressure. The resulting viscous oil was stirred in Et2O (40 mL) for 45 min. The resulting solid was filtered off and washed with Et2O (3×10 mL) to afford the HCl salt as a yellow solid (3.14 g). The crude salt was suspended in 1.0 N NaOH (100 mL) and stirred at 25 C. for 2 h. The solids were filtered, washed with water (2×10 mL), and dried to afford 2,4-Diamino-5-iodopyrimidine as a brown powder (1.71 g, 80%). An analytical sample was prepared by recrystallization from MeCN to give 2,4-Diamino-5-iodopyrimidine as colorless crystals: Rf=0.25 (9:1, CHCl3:MeOH); mp=212-214 C.; 1H NMR (DMSO-d6) delta 7.92 (s, 1H), 6.40 (s, 2H), 6.10 (s, 2H); 13C NMR (DMSO-d6) delta 162.8, 162.7, 162.0, 61.2; HREI[M+]235.9559 (calculated C4H5IN4: 235.9559); Anal. (C4H5IN4) C, H, N.
1.85 g
With N-iodo-succinimide; acetic acid; In methanol; at 0 - 35℃; for 2h;
a) 5-iodo<strong>[156-81-0]pyrimidine-2,4-diamine</strong> NIS (2.30 g) was added to a mixture of <strong>[156-81-0]pyrimidine-2,4-diamine</strong> (1.12 g), acetic acid (20 mL) and methanol (20 mL) at 0 C. The mixture was stirred at room temperature for 2 hr. The reaction mixture was quenched with a saturated aqueous sodium thiosulfate solution at 0 C., and neutralized with 8N aqueous sodium hydroxide solution. The precipitate was collected by filtration and washed with water to give the title compound (1.85 g). 1H NMR (300 MHz, DMSO-d6) delta 6.07 (2H, s), 6.35 (2H, brs), 7.92 (1H, s).
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