{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,9,16]],"date-time":"2024-09-16T18:28:17Z","timestamp":1726511297771},"reference-count":16,"publisher":"CLOCKSS Archive","issue":"3","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["HETEROCYCLES"],"published-print":{"date-parts":[[2001]]},"DOI":"10.3987\/com-00-9142","type":"journal-article","created":{"date-parts":[[2009,3,9]],"date-time":"2009-03-09T04:44:44Z","timestamp":1236573884000},"page":"461","source":"Crossref","is-referenced-by-count":3,"title":["A New Sandmeyer Iodination of 2-Aminopurines in Non-aqueous Conditions: Combination of Alkali Metal Iodide and Iodine as Iodine Sources"],"prefix":"10.13030","volume":"55","author":[{"given":"Naoki","family":"Ozeki","sequence":"first","affiliation":[]},{"given":"Naoyuki","family":"Shimomura","sequence":"additional","affiliation":[]},{"given":"andHitoshi","family":"Harada","sequence":"additional","affiliation":[]}],"member":"5187","reference":[{"key":"10.3987\/COM-00-9142-1","unstructured":"1. O. Asano, H. Harada, Y. Hoshino, S. Yoshikawa, T. Inoue, T. Horizoe, N. Yasuda, K. Nagata, J. Nagaoka, M. Murakami, and S. Kobayash, (Eisai Co., Ltd.). Jpn. Kokai Tokkyo Koho, 99 263,789, 1999 (Chem. Abstr., 1999, 131, 116251)."},{"key":"10.3987\/COM-00-9142-2","unstructured":"2. R. F. Heck, Acc. Chem. Res. 1979, 12, 146."},{"key":"10.3987\/COM-00-9142-3","unstructured":"3. K. Sonogashira, Y. Tohda, and N. Hagihara, Tetrahedron Lett., 1975, 50, 4467."},{"key":"10.3987\/COM-00-9142-4","unstructured":"4. T. Sandmeyer, Ber., 1884, 17, 1633, 2650."},{"key":"10.3987\/COM-00-9142-5","unstructured":"5. T. Sakamoto, Y. Kondo, M. Uchiyama, and H. Yamanaka, J. Chem. Soc., Perkin Trans.1, 1993, 1941."},{"key":"10.3987\/COM-00-9142-6","unstructured":"6. H. Zollinger, \u201cAzo and Diazo Chemistry\u201d, Interscience, New York, 1961; S. Patai., Ed, \u201cThe Chemistry of Diazonium and Diazo Groups\u201d, Part 2, pp. 645, Wiley, Bristol, 1978."},{"key":"10.3987\/COM-00-9142-7","doi-asserted-by":"crossref","unstructured":"7. L. Friedman, and J. F. Chlebowski, J. Org. Chem., 1968, 33, 1636; M. P. Doyle, B. Siegfried, and J. F. Dellaria Jr., J. Org. Chem., 1977, 42, 2426; N. Takamura, T. Mizoguchi, K. Koga, and S. Yamada, Tetrahedron, 1975, 31, 227.","DOI":"10.1021\/jo01268a069"},{"key":"10.3987\/COM-00-9142-8","doi-asserted-by":"crossref","unstructured":"8. V. Nair, and S. G. Richerdson, Synthesis, 1982, 670.","DOI":"10.1055\/s-1982-29896"},{"key":"10.3987\/COM-00-9142-9","doi-asserted-by":"crossref","unstructured":"9. A. Matsuda, M. Shinozaki, T. Yamaguchi, H. Homma, R. Nomoto, T. Miyasaka, Y. Watanabe, and T. Abiru, J. Med. Chem., 1992, 35, 241.","DOI":"10.1021\/jm00080a007"},{"key":"10.3987\/COM-00-9142-10","unstructured":"10. H. Suzuki, and N. Nonoyama, Tetrahedron Lett., 1998, 39, 4533."},{"key":"10.3987\/COM-00-9142-11","unstructured":"11. P. Diaz, S. Michel, L. Stella, and B. Charpenter, Bioorg. Med. Chem. Lett., 1997, 7, 2289."},{"key":"10.3987\/COM-00-9142-12","unstructured":"12. Since the 6-amino group of adenosine derivative was reductively deaminated to nebularine derivatives in THF with n-pentyl nitrite,14 the reductive deamination of the 2-amino group of 2 can be explained by a similar mechanism."},{"key":"10.3987\/COM-00-9142-13","unstructured":"13. This compound may be formed by reaction of the proposed 2-purinyl radical intermediate of the diazotization reaction8, 15 with MeCN, followed by H2O addition."},{"key":"10.3987\/COM-00-9142-14","doi-asserted-by":"crossref","unstructured":"14. V. Nair, and S. D. Chamberlain, Synthesis, 1984, 401.","DOI":"10.1055\/s-1984-30851"},{"key":"10.3987\/COM-00-9142-15","unstructured":"15. V. Nair, and S. G. Richerdson, J. Org. Chem., 1980, 45, 3969."},{"key":"10.3987\/COM-00-9142-16","unstructured":"16. The general procedure of our method is as follows; isopentyl nitrite (2.9 mL, 21.8 mmol) was added to a mixture of 6-chloro-8-(3-fluorophenyl)-9-methyl-9H-purin-2-amine (2, 1.0 g, 3.6 mmol), CsI (0.94 g, 3.6 mmol), I2 (0.46 g, 1.8 mmol), and CuI (0.21 g, 1.1 mmol) in DME (20 mL). The mixture was heated at 60-65\u00b0C for 1.5 h, and then cooled to rt. Insoluble materials were removed by filtration, and the filtrate was diluted with toluene (30 mL), washed with 25% aq. NH3 (10 mL x 2), 5% aq. Na2S2O3 (10mL) and then 5% aq. NaCl (5 mL), dried over MgSO4, followed by evaporation of the solvent to give a slightly yellowish white solid. The solid was crystallized from toluene (10 mL) and n-heptane (20 mL) at 0\u00b0C, filtered, and then washed with toluene (10 mL) to give 6-chloro-8-(3-fluorophenyl)-2-iodo-9-methyl-9H-purine (1, 1.19 g, 85 %) as white powder: mp 185.7\u00b0C (recrystallized from toluene : n-heptane = 1 : 2). 1H NMR (DMSO-d6, 400 MHz): \u03b4(ppm) 3.89 (s, 3H), 7.49-7.56 (m, 1H), 7.66-7.72 (m, 1H), 7.76-7.82 (m, 2H). MS: (FAB) 389 (MH+)."}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T20:31:37Z","timestamp":1719261097000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-00-9142"},"secondary":[{"URL":"https:\/\/triggered.edinburgh.clockss.org\/ServeContent?doi=10.3987%2Fcom-00-9142","label":"edinburgh"}]},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2001]]},"references-count":16,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2001]]}},"alternative-id":["COM-00-9142"],"URL":"https:\/\/doi.org\/10.3987\/com-00-9142","relation":{},"ISSN":["0385-5414"],"issn-type":[{"type":"print","value":"0385-5414"}],"subject":[],"published":{"date-parts":[[2001]]}}}