4-Amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via 
Mitsunobu Reaction of 4-Amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-Mesyl- and N-Nosylarylamines

Viktoras Masevicius; Grazina Petraityte; Sigitas Tumkevicius

doi:10.1055/s-0031-1290524

Synthesis, Table of Contents

Synthesis 2012; 44(9): 1329-1338
DOI: 10.1055/s-0031-1290524

paper

4-Amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via Mitsunobu Reaction of 4-Amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-Mesyl- and N-Nosylarylamines

Viktoras Masevicius

Vilnius University, Department of Organic Chemistry, Vilnius 03225, Lithuania, Fax: +370(5)2330987 Email: sigitas.tumkevicius@chf.vu.lt

,

Grazina Petraityte

Vilnius University, Department of Organic Chemistry, Vilnius 03225, Lithuania, Fax: +370(5)2330987 Email: sigitas.tumkevicius@chf.vu.lt

,

Sigitas Tumkevicius*

Vilnius University, Department of Organic Chemistry, Vilnius 03225, Lithuania, Fax: +370(5)2330987 Email: sigitas.tumkevicius@chf.vu.lt

› Author Affiliations

Abstract

All articles of this category

Abstract

An efficient method for the synthesis of 4-amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via the Mitsunobu reaction of 4-amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-mesyl- and N-nosylarylamines, and subsequent removal of the mesyl and nosyl groups, has been developed. The influence of substituents in the arylamine moiety on the Mitsunobu reaction was investigated. An unexpected nucleophilic substitution of a nitro group in the reaction of N-({4-amino-2-(methylsulfonyl)furo[2,3-d]pyrimidin-5-yl}methyl)-4-nitro-N-phenylbenzenesulfonamide with sodium methoxide was observed.

Key words

alkylation - sulfonamides - heterocycles - oxidation - nucleophilic aromatic substitution

Full Text

References

References

1a Mitsunobu O, Yamada M. Bull. Chem. Soc. Jpn. 1967; 40: 2380
1b Kumara Swamy KC, Bhuvan Kumar NN, Balaraman E, Pavan Kumar KV. P. Chem. Rev. 2009; 109: 2551

2a Fukuyama T, Jow C.-K, Cheung M. Tetrahedron Lett. 1995; 36: 6373
2b Fukuyama T, Cheung M, Jow C.-K, Hidai Y, Kan T. Tetrahedron Lett. 1997; 38: 5831

3 Ohno H, Aso A, Kadoh Y, Fujii N, Tanaka T. Angew. Chem. Int. Ed. 2007; 46: 6325
4 Quattropani A, Dorbais J, Covini D, Pittet P.-A, Colovray V, Thomas RJ, Coxhead R, Halazy S, Scheer A, Missotten M, Ayala G, Bradshaw C, De Raemy-Schenk A.-M, Nichols A, Cirillo R, Tos EG, Giachetti C, Golzio L, Marinelli P, Church DJ, Barberis C, Chollet A, Schwarz MK. J. Med. Chem. 2005; 48: 7882

5a Jung HH, Floreancing PE. J. Org. Chem. 2007; 72: 7359
5b Zhang X, Campo MA, Yao T, Larock RC. Org. Lett. 2005; 7: 763
5c Golantsov NE, Karchava AV, Yurovskaya MA. Chem. Heterocycl. Compd. 2008; 44: 263 ; and references cited therein

6a Zhang X, Zhou X, Kisliuk RL, Piraino J, Cody V, Gangjee A. Bioorg. Med. Chem. 2011; 19: 3585
6b Marques SM, Enyedy EA, Supuran CT, Krupenko NI, Krupenko SA, Santos MA. Bioorg. Med. Chem. 2010; 18: 5081
6c Lockman JW, Murphy BR, Zigar DF, Judd WR, Slattum PM, Gao Z.-H, Ostanin K, Green J, McKinnon R, Terry-Lorenzo RT, Fleischer TC, Boniface JJ, Shenderovich M, Willardsen JA. J. Med. Chem. 2010; 53: 8734

7a Tumkevicius S, Dailide M, Kaminskas A. J. Heterocycl. Chem. 2006; 43: 1629
7b Tumkevicius S, Dodonova J, Kazlauskas K, Masevicius V, Skardziute L, Jursenas S. Tetrahedron Lett. 2010; 51: 3902
7c Tumkevicius S, Dodonova J. Synlett 2011; 1705

8 Masevicius V, Petraityte G, Tumkevicius S. Chem. Heterocycl. Compd. 2009; 45: 357
9 Ryu J.-S. Bull. Korean Chem. Soc. 2006; 27: 631
10 Moskalenko GG, Sedova VF, Mamaev VP. Chem. Heterocycl. Compd. 1989; 25: 919

11a Lis R, Marisca AJ. J. Org. Chem. 1987; 52: 4377
11b Murphy JA, Scott KA, Sinclair RS, Martin CG, Kennedy AR, Lewis N. J. Chem. Soc., Perkin Trans. 1 2000; 2395
11c Pera AL, Leggio A, Liguori A. Tetrahedron 2006; 62: 6100

12a Watanabe T, Takeuchi T, Otsuka M, Tanaka S.-I, Umezawa K. J. Antibiot. 1995; 48: 1460
12b Marvel CS, Helfrick MD, Belsley JP. J. Am. Chem. Soc. 1929; 51: 1272
12c Kamal A, Surendranadha R, Bharathi EV, Dastagiri D. Tetrahedron Lett. 2008; 49: 348
12d Yang S.-M, Scannevin RH, Wang B, Burke SL, Wilson LJ, Karnachi P, Rhodes KJ, Lagu B, Murray WV. Bioorg. Med. Chem. Lett. 2008; 18: 1135
12e Inoue J, Cui Y.-S, Sakai O, Nakamura Y, Kogiso H, Kador PF. Bioorg. Med. Chem. 2000; 8: 2187
12f Zheng X, Oda H, Takamatsu K, Sugimoto Y, Tai A, Akaho E, Ali HI, Oshiki T, Kakuta H, Sasai K. Bioorg. Med. Chem. 2007; 15: 1014
12g Li Q, Sham H, Woods KW, Steiner BA, Gwaltney SL II, Barr KJ, Imade HM, Rosenberg S. US Patent 6521658 B1, 2003
12h Kettler K, Sakowski J, Wiesner J, Ortmann R, Jomaa H, Schitzer M. Pharmazie 2005; 60: 323
12i Adams R, Werbel LM. J. Am. Chem. Soc. 1958; 80: 5799