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. 5719-08-4, name is 4-Chloro-9H-pyrimido[4,5-b]indole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H6ClN3
3.9. 4,6-Dichloro-9-(2,3,5-tri-O-benzoyl-b-D-ribofuranosyl)-pyrimido[4,5-b]indole (13) : Pyrimidoindole 11 (200 mg, 0.84 mmol) was suspended in acetonitrile (5 ml) and BSA (206 ll, 0.84 mmol) was added. Reaction mixture was stirred for 10 min at rt., TMSOTf (308 ll, 1.68 mmol) and protected ribofuranose (430 mg, 0.84 mmol) were added. Mixture was heated to 60 C for 8 h. After cooling to rt, the mixture was extracted with EtOAc and water, organic layer was washed with NaHCO3 and again with water, dried over MgSO4 and evaporated under reduced pressure. Crude product was purified using column chromatography (hexane/EtOAc, 0-40% EtOAc). After crystallization from chloroform/methanol mixture, nucleoside 13 (572 mg, 54%) was observed as white crystals; 3.10 4-Chloro-9-(2,3,5-tri-O-benzoyl-beta-d-ribofuranosyl)-pyrimido[4,5-b]indole (14) : Compound 14 was prepared as described for 13 from pyrimidoindole 12 (300 mg, 1.5 mmol) to give 440 mg (46%) of white crystals; mp 178-182 C, IR (ATR): nu = 2360, 2336, 1718, 1546, 1442, 1261, 1090, 1068, 704 cm-1. H NMR (600.1 MHz, DMSO-d6): 4.69 (dd, 1H, Jgem = 12.4, J5’b,4′ = 4.2, H-5’b); 4.85 (dd, 1H, Jgem = 12.4, J5’a,4′ = 3.2, H-5’a); 4.91 (ddd, 1H, J4′,3′ = 6.6, J4′,5′ = 4.2, 3.2, H-4′); 6.36 (t, 1H, J3′,2′ = J3′,4′ = 6.6, H-3′); 6.61 (dd, 1H, J2′,3′ = 6.6, J2′,1′ = 4.6, H-2′); 7.03 (d, 1H, J1′,2′ = 4.6, H-1′); 7.41 (m, 2H, H-m-Bz-2′); 7.50 (m, 4H, H-m-Bz-3′,5′); 7.51 (ddd, 1H, J6,5 = 7.8, J6,7 = 7.3, J6,8 = 1.0, H-6); 7.57 (ddd, 1H, J7,8 = 8.4, J7,6 = 7.3, J7,5 = 1.3, H-7); 7.62 (m, 1H, H-p-Bz-2′); 7.68 (m, 2H, H-p-Bz-3′,5′); 7.84 (m, 2H, H-o-Bz-2′); 7.93 (m, 2H, H-o-Bz-5′); 7.99 (m, 2H, H-o-Bz-3′); 8.10 (ddd, 1H, J8,7 = 8.4, J8,6 = 1.0, J8,5 = 0.7, H-8); 8.35 (ddd, 1H, J5,6 = 7.8, J5,7 = 1.3, J5,8 = 0.7, H-5); 8.78 (s, 1H, H-2). 13C NMR (150.9 MHz, DMSO-d6): 63.1 (CH2-5′); 70.3 (CH-3′); 72.2 (CH-2′); 78.8 (CH-4′); 86.2 (CH-1′); 112.1 (CH-8); 112.4 (C-4a); 118.0 (C-4b); 122.9 (CH-5); 123.3 (CH-6); 128.6, 128.8 (C-i-Bz); 128.9 (CH-m-Bz); 129.0 (CH-7); 129.3 (CH-o-Bz-5′); 129.4 (C-i-Bz); 129.5 (CH-o-Bz-2′); 129.6 (CH-o-Bz-3′); 133.8, 134.1 (CH-p-Bz); 138.4 (C-8a); 152.1 (C-4); 154.0 (C-2-furyl); 154.0 (CH-2); 155.3 (C-9a); 164.8 (COPh-2′); 165.0 (COPh-3′); 165.5 (COPh-5′). ESI MS m/z (rel.%): 670 (100) [M+Na], 672 (33) [M+2+Na]. HR MS (ESI) for C36H27ClN3O7 [M+H]: calcd 648.15320; found 648.15318.
The synthetic route of 5719-08-4 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Tichy, Michal; Pohl, Radek; Hocek, Michal; Xu, Hao Ying; Chen, Yen-Liang; Yokokawa, Fumiaki; Shi, Pei-Yong; Bioorganic and medicinal chemistry; vol. 20; 20; (2012); p. 6123 – 6133,11;,
Chloride – Wikipedia,
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