Pd/PTABS: An Efficient Water‐Soluble Catalytic System for the Amination of 6‐Chloropurine Ribonucleoside and Synthesis of Alogliptin

Bhilare, Shatrughn; Bandaru, Siva Sankar Murthy; Kapdi, Anant R.; Sanghvi, Yogesh S.; Schulzke, Carola

doi:10.1002/cpnc.58

Cited by 14 publications

(18 citation statements)

References 25 publications

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“…Our goal will also be to implement catalytic protocols for industry relevant productsand in lightof this,a formal synthesis of uracil-based orally administered anti-diabetic drug alogliptin was undertaken(Scheme 14) [42,43]. The synthetic scheme required the conversion of 6-chloropyrimidine-2,4-diol to 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)yl)methyl)benzonitrile in three steps.…”

Section: Amination Reaction Using Pd/ptabsmentioning

confidence: 99%

“…Next, in order to have an efficient water-soluble catalytic system, we developed Pd-imidate based complexes in collaboration with the Serrano group, which were successfully utilized for Heck and Suzuki-Miyaura cross-coupling reactions [36][37][38]. Subsequently, we also developed triazaphosphaadamantane (PTA) based water-soluble phosphines, which are used in combination with palladium acetate for C-C and C-heteroatom bond forming reactions [39][40][41][42][43]. To minimize the duplication in structures, we will abbreviate the sugar units in forthcoming structures, as depicted in Figure 3.…”

Section: Introductionmentioning

confidence: 99%

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Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

Bhilare

Shet

Sanghvi³

et al. 2020

Molecules

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Nucleic acid derivatives are imperative biomolecules and are involved in life governing processes. The chemical modification of nucleic acid is a fascinating area for researchers due to the potential activity exhibited as antiviral and antitumor agents. In addition, these molecules are also of interest toward conducting useful biochemical, pharmaceutical, and mutagenic study. For accessing such synthetically useful structures and features, transition-metal catalyzed processes have been proven over the years to be an excellent tool for carrying out the various transformations with ease and under mild reaction conditions. Amidst various transition-metal catalyzed processes available for nucleoside modification, Pd-catalyzed cross-coupling reactions have proven to be perhaps the most efficient, successful, and broadly applicable reactions in both academia and industry. Pd-catalyzed C–C and C–heteroatom bond forming reactions have been widely used for the modification of the heterocyclic moiety in the nucleosides, although a single catalyst system that could address all the different requirements for nucleoside modifications isvery rare or non-existent. With this in mind, we present herein a review showcasing the recent developments and improvements from our research groups toward the development of Pd-catalyzed strategies including drug synthesis using a single efficient catalyst system for the modification of nucleosides and other heterocycles. The review also highlights the improvement in conditions or the yield of various bio-active nucleosides or commercial drugs possessing the nucleoside structural core. Scale ups wherever performed (up to 100 g) of molecules of commercial importance have also been disclosed.

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Section: Amination Reaction Using Pd/ptabsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

Bhilare

Shet

Sanghvi³

et al. 2020

Molecules

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“…It proceeded smoothly to completion providing 92 % of the desired trifluoroacetate salt of alogliptin (Scheme 4). [42b] …”

Section: Derivatization Of Pta and Applications In Catalysismentioning

confidence: 99%

1,3,5‐Triaza‐7‐phosphaadamantane (PTA) Derived Caged Phosphines for Palladium‐Catalyzed Selective Functionalization of Nucleosides and Heteroarenes

Bandaru

Bhilare

Schulzke

et al. 2020

The Chemical Record

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Phosphines have, in combination with transition metals, played a pivotal role in the rapid development of efficient catalytic processes. Caged phosphines constitute a class of three‐dimensional scaffolds providing unique control over steric and electronic properties. The versatility of the caged phosphine ligands has been demonstrated elegantly by the groups of Verkade, Gonzalvi as well as Stradiotto. Our research group has also been working extensively for the past several years in the development of 1,3,5‐triaza‐7‐phosphaadamantane‐based caged ligands and in this personal note we have summarized these applications pertaining to the modification of biologically useful nucleosides and heteroarenes.

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“…coupling reactions such as Heck, Suzuki-Miyaura and Sonogashira reactions, 36 as well as room-temperature amination, 39,40 low-temperature etherification 41 and C-H bond functionalization of 1,3,4-oxadiazoles. 42 We envisaged the use of Pd(OAc) 2 as a catalyst precursor in combination with PTABS for this current protocol, and to our delight, obtained an improved yield (80%) of the amidederivatized product (Table 1, entry 5).…”

Section: Syn Thesismentioning

confidence: 99%

Pd/PTABS: An Efficient Catalytic System for the Aminocarbonylation of a Sugar-Protected Nucleoside

et al. 2019

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A highly efficient and mild protocol for the aminocarbonylation of a nucleoside is developed by employing palladium/(1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate (Pd/PTABS) as the catalytic system. The developed aminocarbonylation methodology employs CO gas at a relatively low temperature of 60 °C and is suitable for a wide range of amines, including (heteroaryl)benzylic, aliphatic acyclic, alicyclic and secondary amines. This protocol is also utilized for the synthesis of a sangivamycin precursor by carrying out the Pd-catalyzed amination and aminocarbonylation simultaneously. The utility of this protocol is further demonstrated by the synthesis of the drugs moclobemide and nikethamide.

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Pd/PTABS: An Efficient Water‐Soluble Catalytic System for the Amination of 6‐Chloropurine Ribonucleoside and Synthesis of Alogliptin

Cited by 14 publications

References 25 publications

Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes

1,3,5‐Triaza‐7‐phosphaadamantane (PTA) Derived Caged Phosphines for Palladium‐Catalyzed Selective Functionalization of Nucleosides and Heteroarenes

Pd/PTABS: An Efficient Catalytic System for the Aminocarbonylation of a Sugar-Protected Nucleoside

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