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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]

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Meeeee 8 Meeeeeeee Meeeeeeee Meeeeee

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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.

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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]