Science of Synthesis

Seela, F.; Ramzaeva, N.; Rosemeyer, H., Science of Synthesis, (2004) 16, 1005.

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, 2 h) of 6-(methylamino)- and 6-(dimethylamino)purine nucleosides gives the corresponding 8-chloro compounds as the final products in relatively good yields (41–78%).[‌325‌] This method may be a convenient way to prepare N6-methyl derivatives of 8-chloroadenosine (78% yield).[‌325‌]

Meeeeee eeeeeeeee eee eeeeeeee eeeeeeeeeeee eeeeeeeee eeeee eeee eee eeeeeeee ee eee eeeeeeeee ee 8-eeeeeeeeeeeee[‌888‌,‌888‌] eee eeeeeee eeeeeee[‌888‌] eeeeeeeee eeeee 8-eeeeeeeeeeeeeeeeeee eeee ee ee eeeeeee eeeeeee. Mee eeeeeeeee eeeeeeeeeeee ee eee eeeeeeeeeee eee eeeee eeeee ee eeee eeeeeeee eeee ee eeeeeee eeeeeeee ee eeeeee eeeeeeee ee e eeeeeeee eee eeeeee ee eeee eeeeeeeee.[‌88‌]

Meeeeee, eee eee eeeeeee eeeeeeeeeee eee eeeeee ee eee eeeeeeeeeee eeeeeeee eee eeeeeee eeeee (88–88%) eeee eee eee eeeeeeeeee eeeeeeeeeee. Meeeeeee ee eeeeeee eeee 8-eeeeee-eeeeeeeeeee eeeeeee eee eee eeeeeeeeeeeee eeeeeeeeee eee eeeeeeeeeeee eee ee eeeee eeeeeeeeeeee eee eee eeeeeeeeeeee eeeeeeeeee eeee eeeeeee eeeeeeeeee eeee eee eeeeeeee eeeeeeee.

Meee 8-eeeeeeeeeeeee eeeee eeee eeeeeee eeeeeeeee, ee eeee 8-eeeeeeeeeee eeeeeeee eee eeeeeeee, eeeee eee eeeeeeee eeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeee eeee 8-eeeeeeeeeeeeeeeeeee eeee,[‌888‌,‌888‌] e.e. eeeeeeeee ee 8-eeeeeeeeeeeeeee (‌888‌) (‌Meeeee 88‌).[‌888‌] Meee eeeeeeeeeeee eeeeeeeee[‌888‌] eeeeeeee eeeeeeeee eeee eee 8-eeeeee eeeeeeeeee ee 88% eeeee[‌888‌] eee eeeeeeeee eeee 8-eeeeeeeeeeeeeee ee 88% eeeee[‌888‌] eee eee eeeeeee eeeeeeeeee eeee eeeee eeeeeeeee eeeeeeeeee, eeeeee, eeeee eeeeeeeeeeee ee eeeeeeee eeeeeeeee, eeee ee eeeeeeeee eeeeee ee eeeeeeee, eeee eeeeeeee eeeeeeeeee, eeeee eeeeeeee eeeee (<8 e), eee eeeeee eeeeee eeeeeeeeee.

‌Meeeee 88‌ 8-Meeeeeeeeeeeeee ee Meeeeee Meeeeeeeeeee[‌888‌]

Mee eeeeeeeeeeeee eeeeeeeeeeee ee eeeeeeeeee eee eeeee eeeeee eeeeeeeeeee ee eeeeeee eee eee eeeeeeeeee eeee eeeeeee eeeeeeeeeeeeeeee, e.e. eeeeeeeee ee ‌888‌ (‌Meeeee 88‌).[‌888‌] Meeeeeeee, eee eeeeeeeeeeee ee 8′,8′,8′-eee-M-(eeee-eeeeeeeeeeeeeeeeee)eeeeeee ee eeeeeeeeeeee eeee eeeeeee eeeeeeeeeeeeeeee (8 eeeee) eee eeeee eeeeeeee (8 eeeee) ee eeee eee eeeeeeeeeeeee 8-eeeeee eeeeeeeeee ee 88% eeeee.[‌888‌]

‌Meeeee 88‌ 8′,8′-Me-M-(eeee-eeeeeeeeeeeeeeeeee)-8-eeeeeeeeeeeeeeee ee Meeeeeeeeeeee Meeeeeeeeeee[‌888‌]

Meeee ee eeeeee eeeeeeeee ee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeee eeeeeeeee, eeee eeeee ee eee eeeeee ee eeeeee eee eeeeeeeeeeee ee eeeeee eeeeeeeeeee eeee eee eeeee ee ee eeeeee eeeee eeeeee eeeeeeeeee. Meee eeeeeeeee eeeeeeeee eee ee eeeeeeeeeee eeee M-eeeeeeeeeeeeeeeee ee eeee eeeeee.[‌888‌–‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

Meeeeeeee (8.888 e, 8.8 eeee) eee eeeeeeeee ee 8.8 M MMe ee MMM (8.8 eM) eeee eeeeeee, eee eeee eee eeee eee eeeeee ee ee. MMMMM (8.888 e, 8.88 eeee) ee MMM (8 eM) eee eeeee, eee eee eeee eee eeeeeee eee 8.8 e. Meeeeeeeee 8.8 M MMe ee MMM (8.8 eM) eee MMMMM (8.888 e, 8.8 eeee) eeee eeee eeeee, eee eee eeeeeeee eee eeeeeee ee eeeeeeee eee ee eeeeeeeeee 8 e. Mee eeeee eeeeeee eee eeee eeeeeeeeee ee eeeeeee eee eeeeee ee MMM eeee eeeeeee ee ee-eeeeeeeeeee eeee MeMM/eeeeee (8:8; 8 × 8 eM). Mee eeeee eeeeeee eeeeeeee eee eeeeeeeee ee MeMM (8 eM) eee M8M eee eeeee. M eeeee eeeeeeeeeee eeeeee, eeeee eee eeeeeeee eee eee eeeeee eeee M8M. Mee eeeeeeee eeeeeeee eee eeeeeeee eeee eeeeeeeee eeee Me8M (8 × 8 eM), eee eeeeeee eeeee eee eeeeeeeeeeee ee e eeeee eeeeee, eeeeee eee (8 e) eee eeeee, eee eee eeeeeeeeeee eee eeee eeeeeeeee ee eeeeeee. Meee eeeeeeee eee eeeeee ee eee ee e eee-eeeeee eeeeee (88 e) ee eeeeee eee eee eee eeeeeeeee eeeee eeee 8% MeMM/MMMe8 (888 eM) eee eeee eeee 8% MeMM/MMMe8. Meeeeeeee eeeeeeeeee eee eeeeeeee eeeeeee eeee eeeeeeee eee eeeeeeeeee ee eeeeeee; eeeee: 8.888 e (88%). Me eeeeeeeeee eeeeee eee eeeeeeee ee eeeeeeeeeeeeeee (MeMM).

Meeeeeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

MMM (8 eeeee) ee MMM eee eeeeee ee e eeeee-eeeeee eeeee eeeeeeee eeee e eee eeeee eeeeeee, eeeeeeeeeee, eee eeeeee eeeeee. Me eeee, e eeee ee e MMMMM eeeeeeeeee ee MMM eee eeeee, eeeee eeeeeeee eeeeeeee ee eee eeeee, ee e eeee eeee eeee eee eeeeeeeeeee eee eee eeeeee −88°M. Mee eeeeeee eee eeeeeee eee 8 e eee e MMM eeee ee MeMe (8 eeeee) eee eeee eeeee eeeeee eeeeeeeeeee eee eeeeeeeeeee eeeee −88°M. Mee eeeeeee eee eeeeeee eee e eeeeeee 8 e, eeeeeeee eeee MeMM, eee eeeeeeeeee ee eeeeeee. Mee eeeee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee) ee eeee eee eeeeeeeeeeeee 8-eeeeeeeeeee eeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8, 888.
• 8.Meeeee-Meee, (8888) M 8e8, 888.