Article ; Online: An Efficient Microwave Assisted Copper Catalyzed C-3 Amination of 3-Bromopyrazolo[1,5–a]pyrimidine
Tetrahedron Letters. 2023 Feb. 04, p.154393-
2023 , Page(s) 154393–
Abstract: Treatment of 3-bromopyrazolo[1,5–a]pyrimidine with a variety of 1° or 2° alkylamines with 20 mol% CuI, 40 mol% L-proline, and Et₃N (2 equiv) in DMSO under microwave heating at 130 °C (4 hours) gave the corresponding C-3 aminated products in good to ... ...
Abstract | Treatment of 3-bromopyrazolo[1,5–a]pyrimidine with a variety of 1° or 2° alkylamines with 20 mol% CuI, 40 mol% L-proline, and Et₃N (2 equiv) in DMSO under microwave heating at 130 °C (4 hours) gave the corresponding C-3 aminated products in good to excellent isolated yields (54–90%; ave. yield = 77%). The reaction worked well for simple 1° alkylamines (e.g. butylamine, benzylamine, cyclohexylamine, and isopropylamine), and 1° amines with CH₂- or CH₂CH₂-linked heterocycles (e.g. furan, thiophene, pyridine, and/or indole) were also well tolerated. 2° Alkylamines were also good substrates for this reaction (e.g. piperidine, pyrrolidine, and morpholine). The reaction worked well under conventional heating conditions on both the mg or gram-scales, with representative gram-scale reactions giving products in 72-76% yield under conventional heating. Coupling to a pegylated azide (11-azido-3,6,9-trioxaundecan-1-amine, 65% yield microwave) demonstrated compatibility of this coupling methodology for potential click-type conjugation of the pyrazolo[1,5–a]pyrimidine to biologically relevant target ligands. |
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Keywords | amination ; azides ; benzylamines ; butylamine ; furans ; heat ; indoles ; ligands ; morpholine ; piperidines ; proline ; pyridines ; thiophene ; Pyrazolo[1,5–a]pyrimidine ; 3-Bromopyrazolo[1,5–a]pyrimidine ; Copper catalyzed amination |
Language | English |
Dates of publication | 2023-0204 |
Publishing place | Elsevier Ltd |
Document type | Article ; Online |
Note | Pre-press version |
ZDB-ID | 204287-3 |
ISSN | 1873-3581 ; 0040-4039 |
ISSN (online) | 1873-3581 |
ISSN | 0040-4039 |
DOI | 10.1016/j.tetlet.2023.154393 |
Database | NAL-Catalogue (AGRICOLA) |
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