These common heterocyclic compound, 3718-88-5, name is 3-Iodobenzylamine hydrochloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 3718-88-5
Example 41 This example describes the synthesis of N6 -(3-iodobenzyl)-9-[beta-D-ribofuranosyl]-adenine. A mixture of 6-chloropurine riboside (Aldrich Chemical Co., 100 mg, 0.35 mmol), triethylamine (0.146 ml, 1.05 mmol), and 3-iodobenzylamine hydrochloride (103 mg, 0.38 mmol) in ethanol (2 ml) was heated for 18 h at 85 C. in a sealed bottle. After the reaction mixture was concentrated to dryness, the residue was purified on a silica gel column chromatography (CHCl3 –MeOH, 10:1) to yield N6 -(3-iodobenzyl)-9-[beta-D-ribofuranosyl]-adenine (148 mg, 88%) as a colorless solid: m.p. 172 C.; 1 H NMR (DMSO-d6) d 3.54 (m, 1H, H-5’a), 3.67 (m, 1H, H-5’b), 3.96 (d, J=3.3 Hz, 1H, H-4′), 4.14 (m, 1H, H-3′), 4.60 (m, 1H, H-2′), 4.66 (br s, 2H, CH2), 5.16 (d, J=4.4 Hz, 1H, exchangeable with D2 O, 3′-OH), 5.34 (br s, 1H, exchangeable with D2 O, 5′-OH), 5.43 (d, J=6.1 Hz, 1H, exchangeable with D2 O, 2′-OH), 5.89 (d, J=6.0 Hz, 1H, H-1′), 7.11 (pseudo t, J=8.0 and 7.8 Hz, 1H, H-5″), 7.36 (d, J=7.6 Hz, 1H, H-4″ or -6″), 7.58 (d, J=7.8 Hz, 1H, H-4″ or -6″), 7.72 (s, 1H, H-2″), 8.21 (s, 1H, H-2 or 8), 8.40 (s, 1H, H-2 or 8), 8.48 (br s, 1H, exchangeable with D2 O, N6 H,).
The synthetic route of 3-Iodobenzylamine hydrochloride has been constantly updated, and we look forward to future research findings.
Reference:
Patent; The United States of America as represented by the Department of Health and Human Services; US5773423; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com