In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 123240-66-4, name is N-(4,6-Dichloropyrimidin-5-yl)formamide, the common compound, a new synthetic route is introduced below. category: pyrimidines
4.3 (1S?,2S?,4S?)-4-(6-Chloro-9H-purin-9-yl)bicyclo[2.2.1]heptan-2-ol (9) A solution of 7 (2.3 g, 14 mmol), 4,6-dichloro-5-aminopyrimidine (3.4 g, 21 mmol) and DIPEA (7.9 mL, 56 mmol) in n-butanol (80 mL) was heated in a sealed microwave vessel at 160 C for 4 h. The resulting reaction intermediate was purified by chromatography on silica gel (toluene-ethyl acetate = 1:4), dissolved in a mixture of triethyl ortoformate (300 mL) and concd HCl (4 mL) and stirred at room temperature for 3-5 d, and then evaporated. This oily residue was dissolved in a mixture of THF and 1M hydrochloric acid (1:1, 125 mL) and stirred at rt for 4 h. After neutralization with sodium hydrogencarbonate, all volatiles were evaporated and the product was purified by column chromatography (ethyl acetate-toluene-acetone-ethanol 17:4:3:1) and crystallization from a toluene-cyclohexane mixture to afford 9 (2.1 g, 55%) as white crystals (mp = 155-157 C). 1H NMR (500 MHz, DMSO): delta 1.35 (dddd, 1H, Jgem = 12.4, J6en-5en = 9.2, J6en-5ex = 4.8, J6en-7b = 2.1, H-6endo), 1.75 (dm, 1H, Jgem = 12.4, H-3exo), 1.79 (tdd, 1H, Jgem = J6ex-5ex = 12.3, J6ex-1 = 5.1, J6ex-5en = 4.2, H-6exo), 1.90 (m, 1H, H-5exo), 2.01 (dddd, 1H, Jgem = 11.3, J5en-6en = 9.1, J5en-6ex = 4.1, J5en-7b = 2.3, H-5endo), 2.05 (dm, 1H, Jgem = 9.1, H-7a), 2.19 (dm, 1H, J1-6ex = 5.0, H-1), 2.49 (m, 1H, H-7b), 2.54 (ddd, 1H, Jgem = 12.5, J3en-2 = 6.9, J3en-7a = 2.4, H-3endo), 3.87 (m, 1H, H-2), 4.93 (d, 1H, JOH-2 = 3.5, OH), 8.71 (s, 1H, H-8′), 8.77 (s, 1H, H-2′). 13C NMR (125.8 MHz, DMSO): delta 24.04 (C-6), 32.65 (C-5), 37.57 (C-7), 42.69 (C-1), 45.85 (C-3), 65.17 (C-4), 72.67 (C-2), 131.72 (C-5′), 146.59 (C-8′), 149.37 (C-6′), 151.28 (C-2′), 152.43 (C-4′). ESI MS m/z (%): 265.2 (100) [M+H]. For C12H13N4OCl (262.69): calculated: 54.45; C, 4.95; H, 21.17; N, 13.39; Cl; found: 54.49; C, 5.08; H, 21.26; N, 12.99; Cl.
The synthetic route of 123240-66-4 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Dejmek, Milan; Hrebabecky, Hubert; Sala, Michal; Dracinsky, Martin; Prochazkova, Eliska; Leyssen, Pieter; Neyts, Johan; Balzarini, Jan; Nencka, Radim; Bioorganic and Medicinal Chemistry; vol. 22; 11; (2014); p. 2974 – 2983;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia