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Synlett 2012; 23(9): 1339-1342
DOI: 10.1055/s-0031-1291043
DOI: 10.1055/s-0031-1291043
letter
Addition of Purines to N-Boc Imines Generated in Situ in Water: Efficient Synthesis of Novel Acyclic Purine Azanucleosides
Further Information
Publication History
Received: 19 January 2012
Accepted after revision: 26 March 2012
Publication Date:
14 May 2012 (online)
![](https://www.thieme-connect.de/media/synlett/201209/lookinside/thumbnails/10.1055-s-0031-1291043-1.jpg)
Abstract
A mild, efficient and highly regioselective addition of purine derivatives to N-Boc imines generated in situ in water was developed for the first time. A wide range of novel acyclic purine azanucleosides were synthesized in moderate to high yields through this transformation. This methodology was also appropriate for some other N-heterocycles.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
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- 10 General Procedure for Addition of Purines 1 with α-Amido Sulfones 2: N-Boc α-amido sulfone (0.2 mmol, 1.0 equiv), Na2CO3 (0.3 mmol, 1.5 equiv), and H2O (2 mL) were put in a 10-mL glass vial equipped with a small magnetic stirring bar. To the solution was added purine derivative (0.24 mmol, 1.2 equiv). After stirring for the stipulated time at r.t., the mixture was diluted with H2O (5 mL) and extracted with EtOAc (3 × 25 mL, for 3aa–3ak, 3ca and 3cj) or CHCl3 (3 × 25 mL, for 3ba, 3da, 3ea, 3fa and 3ga). The organic layers were combined, dried over anhyd Na2SO4 and concentrated under reduced pressure. The residue was subjected to silica gel flash chromatography (EtOAc–hexanes, 1:5) to give the pure product
- 11 tert-Butyl Cyclohexyl (2,6-Dichloro-9H-purin-9-yl)methylcarbamate (3aa): yield: 97%; white solid; mp 182.7–183.3 °C. 1H NMR (300 MHz, CDCl3): δ = 8.15 (s, 1 H), 8.83 (br, 1 H), 5.63–5.69 (m, 1 H), 2.33 (br, 1 H), 1.65–2.02 (m, 4 H), 1.37 (s, 9 H), 0.83–1.36 (m, 6 H). 13C NMR (75 MHz, CDCl3): δ = 154.5, 152.6, 152.4, 151.8, 145.7, 131.3, 81.3, 69.4, 40.1, 29.4, 29.1, 28.1, 25.7, 25.2, 25.1. HRMS (ESI): m/z [M + Na]+ calcd for C17H23Cl2N5NaO2: 422.1121; found: 422.1138
For selected examples of amino acid or peptide derivatives of pyrimidines, see:
For selected examples of aza-analogues of ganciclovir/penciclovir or acyclovir, see:
For selected examples of other acyclic azanucleosides, see:
For some recent examples, see: