67490-21-5Relevant academic research and scientific papers
Tf2O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides
He, Qian,Ye, Jian-Liang,Xu, Fang-Fang,Geng, Hui,Chen, Ting-Ting,Chen, Hang,Huang, Pei-Qiang
, (2021/09/28)
Ten types of Tf2O/TTBP-mediated amide transformation reactions were investigated. The results showed that compared with pyridine derivatives 2,6-di-tert-butyl-4-methylpyridine (DTBMP) and 2-fluoropyridine (2-F-Pyr.), TTBP can serve as an alternative amide activation system for the direct transformation of both secondary and tertiary amides. For most surveyed examples, higher or comparable yields were generally obtained. In addition, Tf2O/TTBP combination was used to promote the condensation reactions of 2-(tert-butyldimethylsilyloxy)furan (TBSOF) with both tertiary and secondary amides, the one-pot reductive Bischler-Napieralski-type reaction of tertiary lactams, and Movassaghi and Hill's modern version of the Bischler-Napieralski reaction. The value of the Tf2O/TTBP-based methodology was further demonstrated by the concise and high-yielding syntheses of several natural products.
2,4,6-Tri-tert-butylpyrimidine (TTBP): A cost effective, readily available alternative to the hindered base 2,6-di-tert-butylpyridine and its 4-substituted derivatives in glycosylation and other reactions
Crich,Smith,Yao,Picione
, p. 323 - 326 (2007/10/03)
It is reported that 2,4,6-tri-tert-butylpyrimidine (TTBP), a highly sterically hindered base available through an efficient, cost-effective one pot sequence, is a replacement for 2,6-di-tert-butylpyridine and its 4-substituted analogs in glycosylation rea
The Synthesis of 4(6)-t-Butylpyrimidines from 4(6)-Halopyrimidines by Using Higher-Order Lithium and Magnesium Organocuprate Reagents
Evans, Russell F.,Savage, G. Paul,Gough, Denise A.
, p. 733 - 740 (2007/10/02)
t-Butyllithium and t-butylmagnesium chloride cyanocuprates were used to prepare 4(6)-t-butylpyrimidines from the corresponding 4(6)-halopyrimidines.The highly hindered 2,4,5-tri-t-butyl-6-chloropyrimidine, containing an ortho-di-t-butyl arrangement, was p
Sterically Hindered Bases. Synthesis of 2,4,6-Trisubstituted Pyrimidines
Martinez, A. Garcia,Fernandez, A. Herrera,Alvarez, Roberto Martinez,Losada, M. C. Silva,Vilchez, D. Molero,et al.
, p. 881 - 882 (2007/10/02)
A new method for the synthesis of sterically hindered pyrimidines 7 by the reaction of alkynes 5 with nitriles 6 in the presence of trifluoromethanesulfonic acid is described.The pKa*-values of some of the synthesized pyrimidines 7, which can b
A New and Convenient Synthesis of Alkyl and Aryl Pyrimidines
Martinez, A. Garcia,Herrera, A.,Martinez, R.,Teso, E.,Garcia, A.,et al.
, p. 1237 - 1241 (2007/10/02)
Vinyl triflates 1, which are obtained easily from the corresponding ketones, react in an excess of pure nitrile (80 deg C/20 hours) to form tri- and tetra-substituted alkyl and arylpyrimidines 4 and 5 in good yields (45-87percent).An isomeric mixture of p
