2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 2. C-Alkylation of pyrimidines with Mannich bases and application to the synthesis of trimethoprim and analogs
A new route to 5-(p-hydroxybenzyl)pyrimidines has been developed which utilizes phenolic Mannich bases plus pyrimidines containing at least two activating groups. The products can be alkylated on the phenolic oxygen or on the pyrimidine N-1 atom, depending on conditions. This method has been used to...
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| Veröffentlicht in: | Journal of medicinal chemistry 1980-04, Vol.23 (4), p.379-384 |
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| container_end_page | 384 |
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| container_issue | 4 |
| container_start_page | 379 |
| container_title | Journal of medicinal chemistry |
| container_volume | 23 |
| creator | Roth, Barbara Strelitz, Justina Z Rauckman, Barbara S |
| description | A new route to 5-(p-hydroxybenzyl)pyrimidines has been developed which utilizes phenolic Mannich bases plus pyrimidines containing at least two activating groups. The products can be alkylated on the phenolic oxygen or on the pyrimidine N-1 atom, depending on conditions. This method has been used to prepare trimethoprim, a broad-spectrum antibacterial agent, starting from 2,4-diaminopyrimidine and 2,6-dimethoxyphenol. |
| doi_str_mv | 10.1021/jm00178a007 |
| format | Article |
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This method has been used to prepare trimethoprim, a broad-spectrum antibacterial agent, starting from 2,4-diaminopyrimidine and 2,6-dimethoxyphenol.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00178a007</identifier><identifier>PMID: 6991692</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkylation ; Animals ; Anti-Bacterial Agents - chemical synthesis ; Bacteria - drug effects ; Escherichia coli - drug effects ; Escherichia coli - enzymology ; Folic Acid Antagonists ; In Vitro Techniques ; Mannich Bases ; Microbial Sensitivity Tests ; Rats ; Structure-Activity Relationship ; Trimethoprim - analogs & derivatives ; Trimethoprim - chemical synthesis ; Trimethoprim - pharmacology</subject><ispartof>Journal of medicinal chemistry, 1980-04, Vol.23 (4), p.379-384</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a269t-4a43f053340ead9abea8c592212111cc50ffe44c4213ad48750fe9c2c2a4e8883</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00178a007$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00178a007$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6991692$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Roth, Barbara</creatorcontrib><creatorcontrib>Strelitz, Justina Z</creatorcontrib><creatorcontrib>Rauckman, Barbara S</creatorcontrib><title>2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 2. C-Alkylation of pyrimidines with Mannich bases and application to the synthesis of trimethoprim and analogs</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A new route to 5-(p-hydroxybenzyl)pyrimidines has been developed which utilizes phenolic Mannich bases plus pyrimidines containing at least two activating groups. The products can be alkylated on the phenolic oxygen or on the pyrimidine N-1 atom, depending on conditions. 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C-Alkylation of pyrimidines with Mannich bases and application to the synthesis of trimethoprim and analogs</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1980-04</date><risdate>1980</risdate><volume>23</volume><issue>4</issue><spage>379</spage><epage>384</epage><pages>379-384</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>A new route to 5-(p-hydroxybenzyl)pyrimidines has been developed which utilizes phenolic Mannich bases plus pyrimidines containing at least two activating groups. The products can be alkylated on the phenolic oxygen or on the pyrimidine N-1 atom, depending on conditions. This method has been used to prepare trimethoprim, a broad-spectrum antibacterial agent, starting from 2,4-diaminopyrimidine and 2,6-dimethoxyphenol.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>6991692</pmid><doi>10.1021/jm00178a007</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1980-04, Vol.23 (4), p.379-384 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_75134378 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkylation Animals Anti-Bacterial Agents - chemical synthesis Bacteria - drug effects Escherichia coli - drug effects Escherichia coli - enzymology Folic Acid Antagonists In Vitro Techniques Mannich Bases Microbial Sensitivity Tests Rats Structure-Activity Relationship Trimethoprim - analogs & derivatives Trimethoprim - chemical synthesis Trimethoprim - pharmacology |
| title | 2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 2. C-Alkylation of pyrimidines with Mannich bases and application to the synthesis of trimethoprim and analogs |
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