Science of Synthesis

Seela, F.; Ramzaeva, N.; Rosemeyer, H., Science of Synthesis, (2004) 16, 971.

A series of carbocyclic guanine nucleosides is prepared by the general synthetic approach[‌189‌–‌196‌] starting from 4,6-dichloropyrimidin-2-amine. Firstly, an amine derivative is condensed with 4,6-dichloropyrimidin-2-amine and the resulting 6-chloropyrimidine-2,4-diamine ‌29‌ is reacted with 4-chlorobenzenediazonium chloride to afford the 5-(4-chlorophenyldiazenyl)pyrimidine ‌30‌. This is reduced with zinc in acetic acid to give the pyrimidinetriamine ‌31‌, cyclization of which with triethyl orthoformate gives the chloropurine ‌32‌ (‌Scheme 25‌).[‌189‌–‌192‌] The guanosine analogues are obtained by hydrolysis of ‌32‌ in dilute aqueous sodium hydroxide.

‌Meeeee 88‌ Meeeeeeeeee-Meeeeeeeeee Meeeeeeeeeee Meeeeeeeeee ee Meeeeeeeeee ee Meeeeeeeeeeeeeeeeee eeee Meeee Meeee/Meee Meeeeeee[‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

M8	Meeee (%) ee ‌88‌e	Mee
	88	[‌888‌]
	88	[‌888‌]
	88	[‌888‌]
	88	[‌888‌]

e Meee ‌88‌.

Mee eeeee eeeee/eeee eeeeeee eeeeeeee e eeeeee ee 8-eeeeeeeeeeeeeeee-8,8-eeeeeeee eeee 8-eeeeeeeeeeeee ee eeee eeeee,[‌888‌–‌888‌] eeeeeeeee eeee eeeeeee ee e eeeee-eeeeeeeeee 8-eeeeeeeeeeeeeeeeeeeeeee, eeeee eee eeeee eeeee ee eeeeeee eeeeeeeee eeee eeeeeeee eeeeeeee (88°M, 8 e) ee eee 8-eeeeeeeeeeee eeeeeeeeeee.[‌888‌] Me ee eeeeeeeeee eeee eeeee eee eeee eeeeeeeeee eeee, ee eeeeeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeee ee eeee eeeee. Me ee eeeeeee eee eee eeeeeeeee ee eeeeee ‌88‌ (‌Meeeee 88‌).

‌Meeeee 88‌ M Meeeee Meeeeeeeee ee Meeeeeeeeee ee e 8-Meeeeeeeeeeeeeeeeeeeeee eeee Meeee Meeee/Meeeeeeeeeee Meee[‌888‌]

Meeeeeee eeeeeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeeeee ee ee eeeeeee eeeeeee eeee eeeee eeee ee eeeeeeee eeeeeeeeeee ee eeeeee eeeeeeeee eeee ee ‌88‌ eeeeeeee (‌Meeeee 88‌).[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeee Meeeeeeeeeeeee eeee Meeeeeee Meeeeeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeee Meeeeeeee

8-[8-(Meeeeeeeeeeeeee)eeeeeeee-8-eeee]-8-eeeeee-8M-eeeeee (‌88‌):[‌888‌]

M eeee ee 8-{[8-(eeeeeeeeeeeeeee)eeeeeeee-8-eeee]eeeee}-8-eeeeeeeeeeeeeee-8-eeeee (888 ee, 8.88 eeee) eee 88 M MMe (888 µM) ee MM(MMe)8 (8.8 eM, 88 eeee) eee eeeeeee eee 8 e ee ee. Mee eeeeeee eee eeeeee eee eeee eeeeee eeee eeee M8M (88 eM). Mee eeeeeee eee eeeeeeeeeee (eM 8–8) ee eeeeeeee ee ee MeMMM8 (∼8 eM), eeeeeeeee eeee MeMMe (8 × 88 eM), eeeee (MeMM8), eeeeeeeeee, eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, 88:8, eeeeeeeeeee/MeMMe 8:8 eee eeee 8:8) ee eeee ee eee eeee eeeeeeeeeeee eeee eeeeeeee ee eeee eeeee eeeeeeee; eeeee: 888 ee (88%); ee 88–88°M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 8e8, 888.