Solid-Phase Synthesis of 2,4-Diaminopyrimidines via Lewis Acid-Mediated Aromatic Nucleophilic Substitution

Arvanitis, Elena A.; Chadha, Naresh K.; Pottorf, and Richard S.; Player, Mark R.

doi:10.1021/cc049956m

Cited by 13 publications

(3 citation statements)

References 15 publications

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“…31 Wenschuh et al realized on-resin peptide macrocyclization using N-heteroaromatics such as Trz. 32 Trz aside, a range of halogenated N-heteroaromatics have been exploited for SP SNAr couplings including: chloropyrimidines reacting with resin-bound amines; 33 resin-bound thiols coupled with 3,6-dichloropyridazine afforded aminopyrazidines after aminolysis cleavage from SP; 34 and 2,4,6-triaminopyrimidines were synthesized using SP techniques. 35,36 Given the advantages of both SP and SNAr methodology Grate et al published their iterative strategy for producing SDMs with diverse side-groups using Trz-based BBs (Figure 2).…”

Section: N-heteroaromaticsmentioning

confidence: 99%

Progress, challenges and future directions of heterocycles as building blocks in iterative methodologies towards sequence-defined oligomers and polymers

2021

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Section: N-heteroaromaticsmentioning

confidence: 99%

Progress, challenges and future directions of heterocycles as building blocks in iterative methodologies towards sequence-defined oligomers and polymers

2021

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“…2 It has been noted that the reaction of halogenopyrimidines with amines is the most used and important reaction in pyrimidine chemistry. 3 Much of recent aminolysis work has been driven by the search for biologically active aminopyrimidine derivatives given that aminopyrimidines derivatives are part of marketed drugs 4,5 and figure in recent [6][7][8] studies of possible biological activity. Bioactivity has also been associated with 3-aminopyrrole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Reaction of 3-aminopyrrole with chloropyrimidines to give pyrroloaminopyrimidines

Rosa¹,

Arnold²,

Wright³

et al. 2015

Arkivoc

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Reaction of 3-aminopyrrole with chloropyrimidines occured only at the 3-amino group. The activating group(s) (Cl, NO 2 or CF 3 ), their relative positions (C4/C6, C2, or C5), and the effect of added base (DIPEA) or acetic acid on the course of the reaction, was studied. When chloro groups were present on both C4/C6 and C2, the only or major product was from the displacement of the C4/C6 chloro group. Only in the reaction of 2,4,6-trichloropyrimidine was substitution at C2 competitive with reaction at C6. Both chloro groups of 2,4-dichloro-3-nitropyrimidine were displaced to give a novel compound with three-linked heterocyclic rings. Reactions of less reactive chloropyrimidines appeared to be favored by acid catalysis.

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“…This is the eighth annual review in an ongoing series of comprehensive reviews in combinatorial chemistry highlighting developments in new methodology and synthesis of small molecule libraries . The survey tallies 388 chemical libraries published in 2004, − …”

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confidence: 99%

Comprehensive Survey of Combinatorial Library Synthesis: 2004

Dolle

2005

J. Comb. Chem.

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An exhaustive compilation of biologically active libraries covering the years 1992-1997 was presented in a previous review [1a]. In that review, libraries were divided among 4 major categories, including those active against proteases, non-proteolytic enzymes, Gprotein coupled receptors, and non-G-protein coupled receptors. A generic structure for each library was provided as well as the structure of the most active member. The number of biologically active libraries reported in the literature during this time period (86 total) represents <25% of the total number of published library constructs. Disclosure of library synthesis without accompanying screening data is a more common occurrence. Because these types of libraries are equally important to the practicing combinatorial chemist, it was thought that a comprehensive listing of such libraries spanning the years 1992-1997 would be a useful supplement to the previous review [1a,b].Library constructs [2-248] listed herein are relegated to one of five tables. Table 1 is entitled 'Scaffold derivatization' and includes all constructs in which a multi-functional scaffold is modified in some fashion to create a library. An example of a construct found in Table 1 would be the sequential addition of three nucleophiles to trichloropyrimidine. Table 2, entitled 'Acyclic synthesis', lists all linear constructs such as those derived from multi-component Ugi condensations.

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Solid-Phase Synthesis of 2,4-Diaminopyrimidines via Lewis Acid-Mediated Aromatic Nucleophilic Substitution

Cited by 13 publications

References 15 publications

Progress, challenges and future directions of heterocycles as building blocks in iterative methodologies towards sequence-defined oligomers and polymers

Progress, challenges and future directions of heterocycles as building blocks in iterative methodologies towards sequence-defined oligomers and polymers

Reaction of 3-aminopyrrole with chloropyrimidines to give pyrroloaminopyrimidines

Comprehensive Survey of Combinatorial Library Synthesis: 2004

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