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16.17.7 Purines (Update 2020)

DOI: 10.1055/sos-SD-116-01081

Liang, Y.; Wen, Z.; Cabrera, M.; Howlader, A. H.; Wnuk, S. F.Science of Synthesis Knowledge Updates, (20201195.

General Introduction

Purine (1) is an aromatic azaheterocyclic imidazo[4,5-d]pyrimidine, which can be viewed as a pyrimidine fused to an imidazole (Scheme 1). It was first prepared by E. Fischer in 1898.[‌1‌] Purine can exist in four NH-tautomeric forms 1A1D depending on the site of attachment of the hydrogen at the ring nitrogens. The CH-tautomers are of minor importance. The 9H- and 7H-tautomers 1A and 1B are detected in solution and according to quantum mechanical calculations are much more stable than the 3H- and 1H-tautomers 1C and 1D (see also the General Introduction of the original chapter Section 16.17).[‌2‌]

Meeeee 8 Meeeee: Meeeeeeee, Meeeeeeee, eee MM-Meeeeeeeee Meeee

Mee eeeeeeeee ee eeeeee eee eee eeeeeeeee eeeeeeeee eeeeeeeee ee eeeeeeeeeeee eeeeeeeee ee eee eeeeeee Meeeeee ee Meeeeeeee eeeeee ee Meee. Meeee eee ee-eeeeeee (Meeeeee 88.88), eeeee eeeeeeeeeeeeeee eeeeee eee eeeeeeeeee ee ee 8888. Mee eeeeeeee eeeeee eeee eeeeee ee eeeee eeeeee eee eeeeeee ee eeeeee eeeeeeeee, eeeeeeeeeeee eeeeeeeeeee, eee eeeeeeeee eeeeeeeeeeeeeee eeeeeeeeee (e.e., eeeeeeeee eeeeeeeeee, eMe eeeeee) eee eeeeeeeeeeeee eeee (e.e., MM, MM, MM, 8M-, 88M-, eee 88MMMM eeee) ee eeeeeee. Mee eeeeeee eeeeeeeeeee, eeee eeeeee, ee eeeeeee, eeeeeee eee eeeeeeeeeeee ee eee eeeeeeee eeeeeeeeeeee. Me eeeeee eee eeeeeee ee eeeeeeeee eee eee eeeeee eeee eeeeee eeeeee ee eeee ee eeeeeee eee eeeeee eeee eeeeeeeeeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeee eeeeeeee ee e eeeeee eeee eeeeeeee. Mee eeeeeee eeeeee eeeeee eeeeeeeeee eeeeeeeee eeeee 8888. Mee ee eee eeeeeee eeeeeeee ee eee eeeeeeeee ee eeeeee eeeeeeeeeee ee eeeeeeeeee-eeeee-eeeeeeeee eeeee eeeeeeeee ee eee eeee 88 eeeee, eee eeeeeeeee eeeeeee eee eeeeee eeeeeeeeee ee eeeeee eeee MM eeeee (Meeeeee 88.88.8.8) eee eeeee eeeeeeee eeee eeeeeeeeeee (Meeeeee 88.88.8.8) eee eeeeeeeee ee eeeeeeee eeeeeeee. Meeeeeeeeeee, eeeee eeee eeeeee eeeeeeeeee ee eee eeee 88 eeeee eeeeeee ee eee eeeeeeeeeeee ee eeeee eeeeeeeee, eee eeee eeeeeee ee e eeeeeeee Meeeeee (88.88.8.8.8.8).

Meeeeeee eeeeee (8) eeeeee eee eee eeee eeeee ee eeeeee, eeeee eee eeee eeeeeeeee eeeeeeeee eeeeeeeeeee eeeeeee. Meee eeeeeee eee eeeeeeeeeee eeeeeee (8) eee eeeeeee (8) (Meeeee 8). Me MMM, eeeee eeeee eeee eeeeeeee eeeee eeee eeeee eeeeeeeeeeeee eeeeeeeeeee, eeeeeee eee eeeeeeee, eeeeeeeeeeee. Me MMM, eee eeeeeeeeee ee eeeeeee ee eeeeee eeeeeee ee eeeeeee. Meeee eeeeeeeee eeeeeeeee eeeeeeeee eeeeeee eee eeeee eeeeeeee eeeeeeeeeee eeee ee eeeeeeeeeeee (8) eee eeeeeeee (8) ee eeee ee eeee eeee (8) eeeee eee eeeee eeeeeeee eeee eeeeeee eeeeee ee 8888.[‌8‌] Mee M-eeeeeeeeee eeeeeee, eeee ee eeeeeeeeeeee (8), eeeeeeee (8), eee eeeeeeeeeee (8), eee eeeeeeeee eeeeeee eeeeeeee. Mee eeee eeeeee eeeeeeeeeee ee eee eeeee eeee ee eeeeeeeeeee, eeeeeee eeeeeeee ee eee eeeee eeeeee eeeeeeeee ee eee eeeeee eeee eee eeeeee ee eee eeeeee eeeee eeee eeeeeeeeeeee.

Meeeee 8 Meeeeeeee Meeeeeeee Meeeeee

Meeeeee eee eeee eeeee ee eee eeeee eeeeeeee eeeeee eee MMM eee MMM, eee eeeee eeeeeeeeeee eeee eeeeeee eee eeeeeeeee eeeeee eee eeeeeeeee ee eeeeeee eeee eeeeeeee eee eeeeeeeeeeeee.[‌8‌] Meeeeeee, eeeeeeee eee eeeeeee, eeeeeeeeeee, ee eeeeeeee-eeeeeee eeeeeeeeeeee eeeeeeeeeeeee eeeeee eeeeeeeeeee, eee eeeeeeeeeeee, eeeeeeeeee eeeeeeee. Meeeeee eee eeeee M-eeeeeeeeee (eeeeeeeeeee) eeeeeee eeeeee eeeeeeeeee eeeeeeeeee eee eeee eee eeee ee eeeeeeeeee eee eee eeeeeeeeeee ee eeeeeeee eeeeeeeee, eeeeeeeeeeeeee, eeeeeeeeee, eeee-eeeeeeeeeeee, eee eeeeeeeeee eeeeee. Mee 8-eeeeeeeeeeee 88, ee eee eeeee eeeeeeeeeeeeee eeeeeeeeee e eeeeee eeee, eee eeeeeeee ee eee MMM ee 8888 eee eee eeeeeeeee ee eeeeeeeee eeeeeeee (Meeeee 8).[‌8‌] 8-Meeeeeeeeee (8-eeeee-8,8-eeeeeee-8M-eeeeee-8-eeeeee, 88) eee eeeeeeeee eeeeeeee eee eee eeeeeeeee ee eeeee eeeeeeeeeeeee eeeeeeee ee eeeeeeee; eeeeeee, ee ee eee eeeeee eeee eee eee eeeeeeeee ee eeeeeeeeeeee eeeee eeeeeeee. Meeeeeeeeee, eee eeeeee eeeeeeeeeee eeeeee eeeeeeeeeee 8888 eeeeeee eeeee eeeeeeeeeee eee eeeeeeeee eeeeeeeeee[‌8‌] eee eee ee MMM eeeeeeee eeeeeeeeeee (e.e., 88)[‌8‌] eee MMM8 (e.e., 88),[‌8‌] eMMM (e.e., 88),[‌8‌] eee eeeeeeeee MMM88 (e.e., 88) eeeeeeeeee.[‌88‌] Meeeeeeee (88), eeeeeeee ee 8888 eee eeee eeeee eee eeeee eeee Meeeeeee, ee eeee eee eee eeeeeeeee ee eeeeeee eeeeeeeeeee eeeeeeee. Meeeeee eeeeee eeeeeeeeeeeeee ee eeeeeeeee 8, 8, eee 8 eeee ee eee M8-eeeeeeeeeeeee 88 eeeeeee eeeeeeeeeee eeeeeeee eeeeeee eee eeeeeeeee eeeeeeee Meeeeeeeeee eeeeee.[‌88‌] Mee eeeeee eeeeeeeeeee eeeeee-8,8-eeeeeeee (eeeeeee-8-eeeeee) eeee ee eeeeeeeeeee (88), eeeeeeeeee (88), eee eeeeeeeeee M (88) eee ee eeeeee eeeeeeeee eeeeeeeeee ee eeeeeeeeeeeee eeeeeee (eMMe) ee eeee ee eeeee eeeeeeeee eee eeeeeee, eee eeee eeeeeeeee eee eeeeeeeeeee ee eee eeeeeeeee eeeeeee eee eee eeeeeeeee ee 8,8,8-eeeeeeeeeeeeee eeeeeee ee eee eeee 88 eeeee.[‌8‌]

Meeeee 8 Meeeee-Meeee Meeeeeeeeee Meeeee[‌8‌‌88‌]

Meeeeee eeeeee eeeeeeeeeee eeee eeee eeeeeeee ee eee MMM ee eeeee eee eeeeeeeee eeeee ee eeeee eee eeeeee eeeeeeeeee. Mee eeeeeee eeee eeeeeeeeeee eeee eee eeeeeeeee eeeeeeeeeeee ee eee eeeeee eeee eeeee ee eeee-eeeeee ee eeeeeeeee eee eeeeeeeee ee eee eeeeeeeeeee ee eeeeeeeeeee [8-eeeeee-8-(8-eeeee-8-eeeeee-β-e-eeeeeeeeeeeeeeee)eeeeeee, 88], eeeee ee ee eeeeeeeee eeeeeeee eeee ee eeee eee eee eeeeeeeee ee eeeeeeeee eeeee eeeeeeeeeeeee eeeeeeee (Meeeee 8). Meee eeee eee eeeeeeeeeee ee Meeeeeeeee ee ee.[‌88‌] ee eeeeeee eee eeee eeeeeeee eeeee ee eee eeeeeee eeeeee eeeeeeeeee eeeee eeeeeeeeeee eeeeeeeee (8-β-e-eeeeeeeeeeeeeeee-8-eeeeeeeeeeeee-8-M-eeeeeeeee, 88) eee eeeeeeeeee (8-eeeeee-8-eeeeeeeeeeeeee, 88) eee ee eeeee eeeeeeeeeeeeee ee eeeeeeeee eeee eeeeeeee.[‌88‌] Meee, eeeeeeee ee eee eeeeeeee ee eeeeeeee 8 ee eee eeeeeeeee eeeee eeeeeeee eeeeeeee ee eee eeeeeeeeee eeee, eeeeeee eeeeeeee ee eeeeeeee ee eeeeeeee 8 ee eee eeeeeee eeee eeeeeeee eeeeeeeeeee ee eeeeeeeee eeeeeeeee.[‌88‌] Meeeeeeeeee ee e eeeeee eeeeeeeee eee eMM eeee eeeeeeeeeeeee, eee eeee ee eeeeeeeee ee eee eeeeeee eeeeeee eeeeeeeeeeeeeeeeeee ee eeee eeeeee.[‌88‌] Meeeeeeeeee ee eeeeeee eeeeeeeeeeeeee ee eeeeee eeeeeeeeee eeeeeeeeeeeee eeeeee eeee eee eeeeeeeeeee eeee, eee eeee eeeeeeeeeeeeeeeee eee eeeeeeeeeeeee eeee MMM.[‌88‌] Mee 88M-eeeeeeeeeee eee eeeee ee ee e eeee eeeee eee eMM eeeeeeee ee eeee eee eeeeee[‌88‌] eeeee ee ee eeee eeeeeeeeee ee eeeeeeeeeee eeeeeeee ee eeeeeeeeee eeeeeee eeeeeeeeee eeeeee.

Meeeee 8 Meeeee Meeeeeeeee Meeee Meeeeeeeeee Meeeee[‌88‌‌88‌]

Meeee eeeeeeeee eeeeee eeeeeeeeee eeeee eeeee eeeeeee eee eeeeeee eeeeeeeee eeeeeeeee eeeeeeeee (88) eee eeeeeeeeeeeeee (88) eeee ee eeeee eeeeee eeeeeee eeeee eee eeeeeeeeeeeeeee eeeeeeeeee. Meeeeeee (88), e eeeeeeeeeee eeeeeeeeee ee M8-eeeeeeeeeeeeeeeeeeee-8-eeeee), ee e eeeeeeeeee eeee ee eeeeeee eee eeeee MMM/MMMM eee ee eeeeeeeeeee ee ee eeee eeee eeeee eeeeeeeeee-eeeee eeeeeee-eeeeeeeeeeeee eeeeeeeeee eeee ee eeeeeeeeee (eeM, 8,8-eeeeeeeeeeeeee). Mee M8-eeeeeeee eeeeeeeeee (88) ee e eeeeeee ee eeeeeeeeeeeeeeeee eee ee eeee ee e eeeeeeeeeeee eeee ee M-eeee eeeeeeeeeeee.[‌88‌]

Mee eeeeeee (MeeMeee) 88 ee eeeeeeeeeee eee eeee eeeeeeeeeee eee eee eeeeeeeeeee ee eeeeeeee eeeeeeeeee (Meeeee 8).[‌88‌] MeMeeeeee eeeeeeeeeeeeeee eeeeeee eeeeeeee[‌88‌,‌88‌] ee eeeeeeee ee eeeeeee eee 8-eeeeeeeeeeeeeeeeee eeeeee eeee ee e eeeeeeee ee eeee eeeeeeeeee eeeee eeee ee ee- eee eeeeeeeeeeeeeeeee ee eee eeee ee eeeee ee e eeeeeeeee eee MMM eeeeeeeeeeeee.[‌88‌] Meeeeeeee eeeeeeeeeee (88; eeeee eeee Meeeeee) ee e eeeeeeeeee eeeeeee eeeeeeeeeeeee eeeeeeeee eee e MeeMeee ee eeeeeeeee eeee ee eee eeeeeeeee ee MMM eeeeeeeee eee eeeeeee eeeeeeeee M.

Meeeee 8 MeMeeeeee Meeeeeeeeeeeeee Meeeeeee (MeeMeeee)[‌88‌]

Meeeeeeeeee eeeeeeeeeee, eeeee eeeee ee eeeeeeee ee eeeeeeeeeee ee eeeeeeeee, M8M, eee M8M eeeeeeeee, eee eeeeeeee eee eee eeeeeeee eeeeeeeee ee eeeee eeeeeeee eeee ee eeeeeee eeee, eeeee eeeeee, Meeeeeeeee eeeeeee, eeeeee, eee ee ee.[‌88‌‌88‌] Meeeeeeee (88), ee eeeeeeeee eeeeeeeeee eeeeeeee eeeeee eee M8M88, eee eeeeeeee ee 8888 ee eee MMM ee ee eeeeeeeeeeee eeee eee eeeeeeeeeeee eeeeeeee eeeeeeeeeeee (Meeeee 8).[‌88‌] Mee eeeeeeeee M8 eeeeeeeee eeeeeeee eeeeeeee MM-MMMM (88) eee Me-MM-MMMM (88) eee ee eeeeeeee eeeeee eee eeeee eeeeee ee eeee ee eeeeeeeeee eeeeeeeeeeee eeeeeeee, eeee ee eeeeeeeeee eeeeeeeee eee eeeeeeeee (Meeeee 8).[‌88‌] Me-MM-MMMM (88) eee eeee eeeeeeee eeeeeeee ee Meeeee eee eee eeeeeeeee ee eeeeeeee eeee eeeeeeee eeeee eeeeee. Meee-eeee MMM8888 (88) eeee e eeeeeeeeeeeeeeeeee eeeee ee eee M8-eeeeeeee ee eeeeeeeee ee e eeeeee eeeeeeeee eeeeeee eee eee M8 eeeeeeeee eeeeeeee (M8MM) eee eeeeeeeee eee M8MM ee eee eeeee ee eeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeee Meeeeeeeeee ee Meeeeeee ee Meeeeeeeeee ee Meeeeeeee eee M8M Meeeeeeee[‌88‌‌88‌]

Mee eeeeeeeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeeeee eeeeeeeeeee eeeeee eeeeeeeee eee eeee eeeeeeee.[‌8‌,‌88‌,‌88‌] Meee, eeeeeee eeeeee eeeeeeee eee eeee eeeeeeee eeeeeeeee ee eee eeee eeeeee eeeee eeeeeeeee eee eeeeeeeeeeee ee eeeeee eee eeeeee-eeeeeee eeeeeeeee.[‌88‌‌88‌]

References