-
5
-
-
0037660637
-
-
(c) Byk, G.; Gottlieb, H. E.; Herscovici, J.; Mirkin, F. J. Comb. Chem. 2000, 2, 732.
-
(2000)
J. Comb. Chem.
, vol.2
, pp. 732
-
-
Byk, G.1
Gottlieb, H.E.2
Herscovici, J.3
Mirkin, F.4
-
6
-
-
0037019968
-
-
(d) Dondoni, A.; Massi, A.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2002, 67, 6979.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 6979
-
-
Dondoni, A.1
Massi, A.2
Sabbatini, S.3
Bertolasi, V.4
-
7
-
-
0142123401
-
-
(e) Dzvinchuk, I. B.; Makitruk, T. V.; Lozinskii, M. O. Chem. Heterocycl. Comput. 2003, 39, 455.
-
(2003)
Chem. Heterocycl. Comput.
, vol.39
, pp. 455
-
-
Dzvinchuk, I.B.1
Makitruk, T.V.2
Lozinskii, M.O.3
-
8
-
-
0043032892
-
-
(f) Dondoni, A.; Massi, A.; Minghini E.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2003, 68, 6172.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 6172
-
-
Dondoni, A.1
Massi, A.2
Minghini, E.3
Sabbatini, S.4
Bertolasi, V.5
-
9
-
-
0038742048
-
-
(g) Abelman, M. M.; Smith, S. C.; James, D. R. Tetrahedron Lett. 2003, 44, 4559.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 4559
-
-
Abelman, M.M.1
Smith, S.C.2
James, D.R.3
-
10
-
-
0037273986
-
-
(h) Gong, D.; Zhang, L.; Yuan, C. Heteroatom Chem. 2003, 14, 13.
-
(2003)
Heteroatom Chem.
, vol.14
, pp. 13
-
-
Gong, D.1
Zhang, L.2
Yuan, C.3
-
15
-
-
2342533697
-
-
(m) Bandyopadhyay, C.; Nag, P. P.; Sur, K. R.; Patra, R.; Banerjee, S.; Sen, A.; Ghosh, T. J. Indian Chem. Soc. 2004, 81, 132.
-
(2004)
J. Indian Chem. Soc.
, vol.81
, pp. 132
-
-
Bandyopadhyay, C.1
Nag, P.P.2
Sur, K.R.3
Patra, R.4
Banerjee, S.5
Sen, A.6
Ghosh, T.7
-
16
-
-
3543031001
-
-
(n) Shaabani, A.; Bazgir, A.; Bijanzadeh, H. R. Mol. Div. 2004, 8, 141.
-
(2004)
Mol. Div.
, vol.8
, pp. 141
-
-
Shaabani, A.1
Bazgir, A.2
Bijanzadeh, H.R.3
-
18
-
-
0347928672
-
-
(b) Deres, K.; Schroder, C. H.; Paessens, A.; Goldmann, S.; Hacker, H. J.; Weber, O.; Kraemer, T.; Niewoehner, U.; Pleiss, U.; Stoltefuss, J.; Graef, E.; Koletzki, D.; Masantschek, R. N. A.; Reimann, A.; Jaeger, R.; Groß, R.; Beckermann, B.; Schlemmer, K.-H.; Haebich, D.; Rubsamen-Waigmann, H. Science 2003, 299, 893.
-
(2003)
Science
, vol.299
, pp. 893
-
-
Deres, K.1
Schroder, C.H.2
Paessens, A.3
Goldmann, S.4
Hacker, H.J.5
Weber, O.6
Kraemer, T.7
Niewoehner, U.8
Pleiss, U.9
Stoltefuss, J.10
Graef, E.11
Koletzki, D.12
Masantschek, R.N.A.13
Reimann, A.14
Jaeger, R.15
Groß, R.16
Beckermann, B.17
Schlemmer, K.-H.18
Haebich, D.19
Rubsamen-Waigmann, H.20
more..
-
21
-
-
0028910985
-
-
(b) Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; De Brosse, C.; Mai, S.; Truneh, A.; Gaulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westly, J. W.; Potts, B. C. J. Org. Chem. 1995, 60, 1182.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1182
-
-
Patil, A.D.1
Kumar, N.V.2
Kokke, W.C.3
Bean, M.F.4
Freyer, A.J.5
De Brosse, C.6
Mai, S.7
Truneh, A.8
Gaulkner, D.J.9
Carte, B.10
Breen, A.L.11
Hertzberg, R.P.12
Johnson, R.K.13
Westly, J.W.14
Potts, B.C.15
-
22
-
-
0028939869
-
-
(c) Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. J. Am. Chem. Soc. 1995, 117, 2675.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 2675
-
-
Overman, L.E.1
Rabinowitz, M.H.2
Renhowe, P.A.3
-
24
-
-
0042093870
-
-
Merck & Co., Inc.: Whitehouse Station
-
For representative drugs and biologicals containing pyrimidines (over 80 examples), such as amprolium, bispyribac, cetotiamine, diaveridine, ethirimol, fenarimol, glymidine, ipsapirone, lesopitron, mepanipyrin, nimustine, oxythiamine, peplomycin, quinapyramine, rimsulfuron, sulfabromomethazine,and tandospirone, see: The Merck Index, An Encyclopedia of Chemicals, Drugs and Biologicals, 13th ed.; Merck & Co., Inc.: Whitehouse Station, 2001.
-
(2001)
The Merck Index, An Encyclopedia of Chemicals, Drugs and Biologicals, 13th Ed.
-
-
-
25
-
-
0000482661
-
-
Eynde, J. J. V.; Audiart, N.; Canonne, V.; Michel, S.; Haverbeke, Y. V.; Kappe, C. O. Heterocycles 1997, 45, 1967.
-
(1997)
Heterocycles
, vol.45
, pp. 1967
-
-
Eynde, J.J.V.1
Audiart, N.2
Canonne, V.3
Michel, S.4
Haverbeke, Y.V.5
Kappe, C.O.6
-
26
-
-
0035697361
-
-
Puchala, A.; Belaj, F.; Bergman, J.; Kappe, C. O. J. Heterocycl. Chem. 2001, 38, 1345.
-
(2001)
J. Heterocycl. Chem.
, vol.38
, pp. 1345
-
-
Puchala, A.1
Belaj, F.2
Bergman, J.3
Kappe, C.O.4
-
28
-
-
14544294967
-
-
WO 03006439, 2003
-
(a) Matsushita, A.; Oda, M.; Kawachi, Y.; Chika, J. WO 03006439, 2003.
-
-
-
Matsushita, A.1
Oda, M.2
Kawachi, Y.3
Chika, J.4
-
29
-
-
0031081522
-
-
(b) Watanabe, M.; Koike, H.; Ishiba, T.; Okada, T.; Seo, S.; Hirai, K. Bioorg. Med. Chem. 1997, 5, 437.
-
(1997)
Bioorg. Med. Chem.
, vol.5
, pp. 437
-
-
Watanabe, M.1
Koike, H.2
Ishiba, T.3
Okada, T.4
Seo, S.5
Hirai, K.6
-
30
-
-
17444421249
-
-
Abstracts of Papers, Philadelphia, PA.; American Chemical Society: Washington, DC, ORGN 702
-
For a preliminary communication of this study, see: Kang, F.-A.; Murray, W. V. Abstracts of Papers, 228th National Meeting of the American Chemical Society, Philadelphia, PA.; American Chemical Society: Washington, DC, 2004; ORGN 702.
-
(2004)
228th National Meeting of the American Chemical Society
-
-
Kang, F.-A.1
Murray, W.V.2
-
31
-
-
0032524801
-
-
Hu, E. H.; Sidler, D. R.; Dolling, U.-H. J. Org. Chem. 1998, 63, 3454.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 3454
-
-
Hu, E.H.1
Sidler, D.R.2
Dolling, U.-H.3
-
32
-
-
14544275992
-
-
note
-
6, see the Supporting Information.
-
-
-
-
33
-
-
0025014627
-
-
(a) Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 205
-
-
Coste, J.1
Le-Nguyen, D.2
Castro, B.3
-
34
-
-
0025868658
-
-
(b) Coste, J.; Frerot, E.; Jouin, P. Tetrahedron Lett. 1991, 32, 1967.
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 1967
-
-
Coste, J.1
Frerot, E.2
Jouin, P.3
-
35
-
-
0033051128
-
-
(c) The coupling reactions by directly using commercial PyBOP or PyBroP usually produce about 5% of the pyrolidine-containing side-product 3c (Table 2), which is attributed to the presence of a small amount of pyrrolidine as a contaminant to the commercial phosphonium salts. This side reaction does not occur when the reagents are recrystallized before their use in the coupling reaction. For recrystallization of PyBOP and PyBroP, and a similar observation of pyrolidine-containing side-product formation, see: Alsina, J.; Barany, G.; Albericio, F.; Kates, S. A. Lett. Peptide Sci. 1999, 6, 243.
-
(1999)
Lett. Peptide Sci.
, vol.6
, pp. 243
-
-
Alsina, J.1
Barany, G.2
Albericio, F.3
Kates, S.A.4
-
36
-
-
14544279855
-
-
note
-
PyBOP is slightly less efficient than PyBroP since it forms two transition intermediates with 2, the more reactive 4 (Table 2) and the less reactive 2-O-(benzotriazol-1-yl)-pyrimidine which can be isolated from the incomplete coupling reaction.
-
-
-
-
37
-
-
14544308422
-
-
note
-
It is interesting to note that the less effective solvents, e.g. MeCN, DCM and DMF led to homogeneous reactions, while the more effective solvents, e.g. dioxane, THF and DME, resulted in heterogeneous reactions. Dioxane seems to cause a slightly less heterogeneous, faster and cleaner reaction than THF and DME.
-
-
-
-
38
-
-
0033166435
-
-
It is not surprising that DMF was the least effective solvent for the targeted coupling reaction, since it is known that DMF can form formamidines with amines in the presence of PyBroP; see: Delarue, S.; Sergheraert, C. Tetrahedron Lett. 1999, 40, 5487.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 5487
-
-
Delarue, S.1
Sergheraert, C.2
-
41
-
-
0142147275
-
-
(c) Burke, M. D.; Berger, E. M.; Schreiber, S. L. Science 2003, 302, 613.
-
(2003)
Science
, vol.302
, pp. 613
-
-
Burke, M.D.1
Berger, E.M.2
Schreiber, S.L.3
|