M. Brændvang, L.-L. Gundersen / Tetrahedron Letters 48 (2007) 3057–3059
3059
antimycobacterial purine 7.13 Biological activity of 6
will be published elsewhere.
(k) Smalley, T. L., Jr.; Peat, A. J.; Boucheron, J. A.;
Dickerson, S.; Garrido, D.; Preugschat, F.; Schweiker, S.
L.; Thomson, S. A.; Wang, T. Y. Bioorg. Med. Chem.
Lett. 2006, 16, 2019–2094.
2. Wunder, F.; Tersteegen, A.; Rebmann, A.; Erb, C.;
Farrig, T.; Hendrix, M. Mol. Pharmacol. 2005, 68, 1755–
1781.
Acknowledgement
The Norwegian Research Council is gratefully acknowl-
edged for partial financing of the Bruker Avance instru-
ments used in this study.
3. (a) Chern, J.-H.; Shia, K.-S.; Hsu, T.-A.; Tai, C.-L.; Lee,
C.-C.; Lee, Y.-C.; Chang, C.-S.; Tseng, S.-N.; Shih, S.-R.
Bioorg. Med. Chem. Lett. 2004, 14, 2519–2525; (b) Holla,
B. S.; Mahalinga, M.; Karthikeyan, M. S.; Akberali, P.
M.; Shetty, N. S. Bioorg. Med. Chem. 2006, 14, 2040–2047.
4. For recent reviews, see for instance: (a) Elnagdi, M.;
Al-Awadi, N. In Comprehensive Heterocyclic Chemistry II;
Katritzky, A., Rees, C. W., Scriven, E. F. V., Eds.;
Pergamon Press: Oxford, 1996; Vol. 7, Chapter 7.12, pp
431–477; (b) Dang, Q. Recent. Res. Dev. Org. Chem. 2002,
6, 431–447.
Supplementary data
Spectroscopic data for all new compounds and a proce-
dure for the synthesis of compound 6, can be found in
the supplementary data. Supplementary data associated
with this article can be found, in the online version, at
5. Robins, R. K. J. Am. Chem. Soc. 1956, 78, 784–790.
6. (a) Sugimoto, O.; Sudo, M.; Tanji, K.-i. Tetrahedron 2001,
57, 2133–2138; (b) Sugimoto, O.; Yamada, S.; Tanji, K.-i.
J. Org. Chem. 2003, 68, 2054–2057.
References and notes
7. Zacharie, B.; Connolly, T. P.; Rej, R.; Attardo, G.;
Penney, C. L. Tetrahedron 1996, 52, 2271–2278.
8. (a) Seela, F.; Ramzaeva, N.; Rosemeyer, H. In Science of
Synthesis; Yamamoto, Y., Ed.; Thieme: Stuttgart, 2004;
Vol. 16, pp 945–1108, and references cited therein; For
some recent examples, see for instance: (b) Yang, M.; Ye,
W.; Schneller, S. W. J. Org. Chem. 2004, 69, 3993–3996;
(c) Barral, K.; Courcambeck, J.; Pepe, G.; Balzarini, J.;
Neyts, J.; De Clercq, E.; Camplo, M. J. Med. Chem. 2005,
48, 450–456; (d) Yang, M.; Schneller, S. W.; Korba, B. B.
J. Med. Chem. 2005, 48, 5043–5046; (e) Vina, D.; Santana,
L.; Uriarte, E.; Teran, C. Tetrahedron 2005, 61, 473–478;
(f) Kitade, Y.; Ando, T.; Yamaguchi, T.; Hori, A.;
Nakanishi, M.; Ueno, Y. Bioorg. Med. Chem. 2006, 14,
5578–5583; (g) Yin, X.-q.; Li, W.-k.; Schneller, S. W.
Tetrahedron Lett. 2006, 47, 9187–9189; (h) Aubin, Y.;
Audran, G.; Monti, H. Synlett 2006, 2215–2218.
9. Yang, M.; Zhou, J.; Schneller, S. W. Tetrahedron 2006, 62,
1295–1300.
10. General procedure for N-alkylation of compound 2 under
Mitsunobu conditions: Triphenylphosphine (393 mg,
1.50 mmol) and 4-chloro-1H-pyrazolo[3,4-d]pyrimidine
(2) (154 mg, 1.00 mmol) were dissolved in dry THF
(5 mL) under N2 and cooled to 0 °C for 15 min. The
alcohol (1.00 mmol) was added immediately followed by
dropwise addition of DIAD (300 lL, 1.50 mmol) over
2 min. After stirring at the temperature and time given in
Table 1, silica (1 g) was added and the mixture was
evaporated in vacuo to dryness. The residue was purified
by flash chromatography eluting with EtOAc–hexane
mixtures.
1. See for instance: (a) Burchat, A. F.; Calderwood, D. J.;
Friedman, M. M.; Hirst, G. C.; Li, B.; Rafferty, P.; Ritter,
K.; Skinner, B. S. Bioorg. Med. Chem. Lett. 2002, 12,
1687–1690; (b) Peat, A. J.; Boucheron, J. A.; Dickerson, S.
H.; Garrido, D.; Mills, W.; Peckham, J.; Preugschat, F.;
Smalley, T.; Schweiker, S. L.; Wilson, J. R.; Wang, T. Y.;
Zhou, H. Q.; Thomson, S. A. Bioorg. Med. Chem. Lett.
2004, 14, 2121–2125; (c) Peat, A. J.; Garrido, D.;
Boucheron, J. A.; Schweiker, S. L.; Dickerson, S. H.;
Wilson, J. R.; Wang, T. Y.; Thomson, S. A. Bioorg. Med.
Chem. Lett. 2004, 14, 2127–2130; (d) Scenone, S.; Bruno,
O.; Ranise, A.; Bondavalli, F.; Brullo, C.; Fossa, P.;
Mosti, L.; Menozzi, G.; Carraro, F.; Bernini, C.; Manetti,
F.; Botta, M. Bioorg. Med. Chem. Lett. 2004, 14, 2511–
2517; (e) Borhani, D. W.; Calderwood, D. J.; Friedman,
M. M.; Hirst, G. C.; Li, B.; Leung, A. K. W.; McRae, B.;
Ratnofsky, S.; Ritter, K.; Waegell, W. Bioorg. Med. Chem.
Lett. 2004, 14, 2613–2616; (f) Carraro, F.; Pucci, A.;
Naldini, A.; Scenone, S.; Bruno, O.; Ranise, A.; Bonda-
valli, F.; Brullo, C.; Fossa, P.; Menozzi, G.; Mosti, L.;
Manetti, F.; Botta, M. J. Med. Chem. 2004, 47, 1595–
1598; (g) Scenone, S.; Bruno, O.; Bondavalli, F.; Ranise,
A.; Mosti, L.; Menozzi, G.; Fossa, P.; Manetti, F.;
Morbidelli, L.; Trincavelli, L.; Martini, C.; Lucacchini,
A. Eur. J. Med. Chem. 2004, 39, 153–160; (h) Bookser, B.
C.; Ugarkar, B. G.; Matelich, M. C.; Lemus, R. H.; Allan,
M.; Tsuchiya, M.; Nakane, M.; Nagahisa, A.; Wiesner, J.
B.; Erion, M. D. J. Med. Chem. 2005, 48, 7808–7820; (i)
Carraro, F.; Naldini, A.; Pucci, A.; Locatelli, G. A.;
Maga, G.; Scenone, S.; Bruno, O.; Ranise, A.; Bondavalli,
F.; Brullo, C.; Fossa, P.; Menozzi, G.; Mosti, L.;
Modugno, M.; Tintori, C.; Manetti, F.; Botta, M. J.
Med. Chem. 2006, 49, 1549–1561; (j) Burchat, A.; Borhani,
D. W.; Calderwood, D. J.; Hirst, G. C.; Li, B.; Stachle-
witz, R. F. Bioorg. Chem. Med. Lett. 2006, 16, 118–122;
11. Kamal, A.; Ramesh, G.; Laxman, N. Synth. Commun.
2001, 31, 827–833.
12. See for instance: Knight, D. W.; Leese, M. P. Tetrahedron
Lett. 2001, 42, 2593–2595, and references cited therein.
13. Bakkestuen, A. K.; Gundersen, L.-L.; Utenova, B. T. J.
Med. Chem. 2005, 48, 2710–2723.