Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine
4.1.11 7-(2-O-Acetyl-3,5-di-O-benzyl-4-C-methyl-beta-d-ribofuranosyl)-4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (12) To a slurry of 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine 11 (2.06 g, 12 mmol) in dry MeCN (20 ml) was added N,O-bis(trimethylsilyl)acetamide [BSA] (2.94 ml, 9.55 mmol) and the mixture was stirred at rt for 15 min (clear solution). Then a solution of 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-methyl-beta-d-ribofuranose 5 (5.14 g, 12 mmol) in MeCN (40 ml) was added, followed by TMSOTf (4.34 ml, 24 mmol). The solution was stirred at 80 ¡ãC for 3 h. After cooling, the mixture was diluted with EtOAc (200 ml), cautiously washed with saturated aq NaHCO3 (100 ml) and aqueous phase was re-extracted with EtOAc (2 * 25 ml). Combined organic phases were dried (MgSO4), concentrated in vacuo and loaded on silica by co-evaporation. Column chromatography (SiO2, hexane-AcOEt, 10:1) afforded nucleoside 12 as yellowish oil (3.76 g, 58percent). 1H NMR (500 MHz, CDCl3): 1.32 (s, 3H, CH3-4′); 2.05 (s, 3H, CH3CO); 3.40 (d, 1H, Jgem = 10.2 Hz, H-5’a); 3.56 (d, 1H, Jgem = 10.2 Hz, H-5’b); 4.42 (d, 1H, J3′,2′ = 5.7 Hz, H-3′); 4.48 (bd, 1H, Jgem = 11.5 Hz, CH2a-Bn-5′); 4.50 (d, 1H, Jgem = 11.5 Hz, CH2a-Bn-3′); 4.56 (d, 1H, Jgem = 11.5 Hz, CH2b-Bn-5′); 4.60 (d, 1H, Jgem = 11.6 Hz, CH2b-Bn-3′); 5.56 (bt, 1H, J2′,3′ = J2′,1′ = 5.3 Hz, H-2′); 6.62 (dd, 1H, J1′,2′ = 5.0 Hz, J1′,F = 1.8 Hz, H-1′); 7.29-7.41 (m, 11H, H-o,m,p-Bn-3′,5′, H-6); 8.59 (s, 1H, H-2). 13C NMR (125.7 MHz, CDCl3): 18.99 (CH3-4′); 20.69 (CH3CO); 73.64 (CH2-Bn-5′); 74.18 (CH2-Bn-3′); 74.43 (CH2-5′); 75.97 (CH-2′); 77.79 (CH-3′); 85.00 (CH-1′); 86.30 (C-4′); 107.58 (d, JC,F = 14.4 Hz, C-4a); 109.64 (d, JC,F = 27.0 Hz, CH-6); 127.86 and 127.97 (CH-o-Bn-3′,5′); 128.03 and 128.11 (CH-p-Bn-3′,5′); 128.45 and 128.62 (CH-m-Bn-3′,5′); 137.21 (C-i-Bn-5′); 137.57 (C-i-Bn-3′); 141.60(d, JC,F = 253.6 Hz, C-5); 147.04 (d, JC,F = 1.2 Hz, C-7a); 150.46 (d, JC,F = 3.7 Hz, C-4); 151.50 (CH-2); 169.93 (CO). 19F NMR (470.3 MHz, DMSO-d6): -167.38 (s, 1F, F-5). IR (ATR): nu 1678, 1622, 1593, 1457, 1231, 1070, 1028, 741, 700 cm-1. MS (ESI) m/z 540 (M+H), 562 (M+Na). HRMS (ESI) for C28H27O5N3ClFNa [M+Na] calcd: 562.15155; found: 562.15140.
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Reference:
Article; Nau?, Petr; Caletkova, Olga; Perlikova, Pavla; Po?tova Slav?tinska, Lenka; Tlou??ova, Eva; Hodek, Jan; Weber, Jan; D?ubak, Petr; Hajduch, Marian; Hocek, Michal; Bioorganic and Medicinal Chemistry; vol. 23; 23; (2015); p. 7422 – 7438;,
Pyrimidine | C4H4N2 – PubChem,
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