Synthesis 2017; 49(03): 554-556
DOI: 10.1055/s-0036-1588364
© Georg Thieme Verlag Stuttgart · New York

A Three-Step Protocol towards N-8-(2,2-Dimethoxyethyl)-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one

Kevin Blades*
RedxAnti-infectives, Mereside, Alderley Park, Macclesfield, Cheshire, SK104TG, UK   Email: [email protected]
Steven C. Glossop
RedxAnti-infectives, Mereside, Alderley Park, Macclesfield, Cheshire, SK104TG, UK   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 21 October 2016

Accepted after revision: 06 November 2016

Publication Date:
28 November 2016 (online)


An efficient high-yielding three-step synthesis of N-8-(2,2-dimethoxyethyl)-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one is reported. The route utilises a Heck coupling as the key step.

  • References

  • 1 For lead references, see: Yuan Y, Yang R, Zhang-Negrerie D, Wang J, Du Y, Zhao K. J. Org. Chem. 2013; 78: 5385
  • 2 Barvian M, Boschelli DH, Cossrow J, Dobrusin E, Fattaey A, Fritsch A, Fry D, Harvey P, Keller P, Garrett M, La F, Leopold W, McNamara D, Quin M, Trumpp-Kallmeyer S, Toogood P, Wu Z, Zhang E. J. Med. Chem. 2000; 43: 4606
  • 3 Bifulco NJr, Brooijmans N, Hodous BL, Kim JL, Miduturu CV. Patent WO 2014/011900, 2014
    • 4a Campbell D, Duron SG, Vollrath B, Wade W. Patent WO 2010/071846, 2010
    • 4b Angiolini M, Bassini DF, Gude M, Menichincheri M. Tetrahedron Lett. 2005; 46: 8749
    • 5a Wan Z, Yan H, Hall RF, Lin X, Livia S, Respondek T, Widdowson KL, Zhu C, Callahan JF. Tetrahedron Lett. 2009; 50: 370
    • 5b Kasparee J, Adams JL, Sisko J, Silva DJ. Tetrahedron Lett. 2003; 44: 4567
  • 6 Apsunde T, Wurz RP. J. Org. Chem. 2014; 79: 3260
  • 7 Workup is critical for the isolation of the desired compound, if the reaction is not quenched, excess butoxide anion displaces the thiomethyl group.