Microwave assisted tandem Heck-Sonogashira reactions of N,N-di-Boc-protected 6-amino-5-iodo-2-methyl pyrimidin-4-ol in an efficient approach to functionalized pyrido[2,3-d]pyrimidines

Yang Liu; Shiyu Jin; Zi Wang; Linhua Song; Youhong Hu

doi:10.1021/ol501459e

Microwave assisted tandem Heck-Sonogashira reactions of N,N-di-Boc-protected 6-amino-5-iodo-2-methyl pyrimidin-4-ol in an efficient approach to functionalized pyrido[2,3-d]pyrimidines

Org Lett. 2014 Jul 3;16(13):3524-7. doi: 10.1021/ol501459e. Epub 2014 Jun 23.

Authors

Yang Liu¹, Shiyu Jin, Zi Wang, Linhua Song, Youhong Hu

Affiliation

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 ZuChongZhi Road, Shanghai, 201203, China.

PMID: 24956126
DOI: 10.1021/ol501459e

Abstract

A microwave assisted tandem Heck-Sonogashira cross-coupling reaction between 6-N,N-di-Boc-amino-5-iodo-2-methyl pyrimidin-4-ol and various aryl alkynyl substrates has been developed. This process generates novel 5-enynyl substituted pyrimidines, which can be transformed to novel functionalized pyrido[2,3-d]pyrimidines by way of a silver catalyzed cyclization reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Combinatorial Chemistry Techniques
Cyclization
Microwaves*
Molecular Structure
Pyrimidines / chemical synthesis*
Pyrimidines / chemistry
Silver / chemistry
Stereoisomerism

Substances

Alkynes
Pyrimidines
Silver