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16.17.3.3.2.2 Variation 2: By Chlorination

DOI: 10.1055/sos-SD-016-01192

Seela, F.; Ramzaeva, N.; Rosemeyer, H.Science of Synthesis, (2004161005.

In contrast to the ease of bromination at C8 of purine derivatives, greater difficulty has been noted with regard to chlorination. Attempts at direct chlorination, analogous to bromination, are unsuccessful. However, the direct preparation of 8-chloroadenosine and of its mono- and diphosphate derivatives can be achieved by using tetrabutylammonium iodotetrachloride[‌324‌] and by the use of tert-butyl hypochlorite,[‌325‌] although the yields are low. An analogous chlorination (t-BuOCl, DMF, 70°C, 2h) of 6-(methylamino)- and 6-(dimethylamino)purine nucleosides gives the corresponding 8-chloro compounds as the final products in relatively good yields (4178%).[‌325‌] This method may be a convenient way to prepare N6-methyl derivatives of 8-chloroadenosine (78% yield).[‌325‌]

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References


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