A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular SNAr sequence
A novel tandem reductive amination/intermolecular nucleophilic aromatic substitution （SNAr） sequence has been established for the synthesis of amine containing pyrimidine in formation of one carbon-oxygen and one carbon-nitrogen bonds in a one-pot fashion. Treatment of aldehyde with arylamine, 2-met...
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| Veröffentlicht in: | Journal of Zhejiang University. B. Science 2010-02, Vol.11 (2), p.94-101 |
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| creator | Wu, Hai-feng Zhang, Pei-zhi Wu, Jun |
| description | A novel tandem reductive amination/intermolecular nucleophilic aromatic substitution （SNAr） sequence has been established for the synthesis of amine containing pyrimidine in formation of one carbon-oxygen and one carbon-nitrogen bonds in a one-pot fashion. Treatment of aldehyde with arylamine, 2-methanesulfonyl-4,6-dimeth- oxypyrimidine and sodium borohydride provides good overall yield. The p-toluenesulfonic acid （PTSA） can be used as activator and is generally needed in the reaction. Dioxane is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran （THF）, MeCN, toluene and dichloromethane. The procedure is carried out effectively in the presence of K2CO3. The reaction proceeds smoothly with aromatic aldehydes and arylamines possessing electron-donating or -withdrawing groups. This method can be applied to the synthesis of the oilseed rape herbicide and is superior to the classical one in several aspects： cutting out several purification steps, minimizing solvent use and chemical waste, and saving time. Its advantages such as operational convenience, high-efficient synthesis, and starting material availability make it a desirable method for preparing amines with molecular diversity and biological activity. |
| doi_str_mv | 10.1631/jzus.B0900293 |
| format | Article |
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Treatment of aldehyde with arylamine, 2-methanesulfonyl-4,6-dimeth- oxypyrimidine and sodium borohydride provides good overall yield. The p-toluenesulfonic acid （PTSA） can be used as activator and is generally needed in the reaction. Dioxane is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran （THF）, MeCN, toluene and dichloromethane. The procedure is carried out effectively in the presence of K2CO3. The reaction proceeds smoothly with aromatic aldehydes and arylamines possessing electron-donating or -withdrawing groups. This method can be applied to the synthesis of the oilseed rape herbicide and is superior to the classical one in several aspects： cutting out several purification steps, minimizing solvent use and chemical waste, and saving time. Its advantages such as operational convenience, high-efficient synthesis, and starting material availability make it a desirable method for preparing amines with molecular diversity and biological activity.</description><identifier>ISSN: 1673-1581</identifier><identifier>EISSN: 1862-1783</identifier><identifier>DOI: 10.1631/jzus.B0900293</identifier><identifier>PMID: 20104643</identifier><language>eng</language><publisher>Heidelberg: SP Zhejiang University Press</publisher><subject>Aldehydes ; Amines ; Ar序列 ; Biological ; Biomedical and Life Sciences ; Biomedicine ; Biotechnology ; Cutting ; Derivatives ; Sodium ; Solvents ; Synthesis ; 亲核取代反应 ; 分子间 ; 对甲苯磺酸 ; 简便合成 ; 衍生物 ; 还原胺化</subject><ispartof>Journal of Zhejiang University. B. Science, 2010-02, Vol.11 (2), p.94-101</ispartof><rights>Zhejiang University and Springer Berlin Heidelberg 2010</rights><rights>Copyright © Zhejiang University and Springer-Verlag Berlin Heidelberg 2010</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c429t-4f6edc7c7e2331d2298a9a16b589cfc72eb754a51306ac95a1528a050fc7108e3</citedby><cites>FETCH-LOGICAL-c429t-4f6edc7c7e2331d2298a9a16b589cfc72eb754a51306ac95a1528a050fc7108e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://image.cqvip.com/vip1000/qk/86281A/86281A.jpg</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2816312/pdf/$$EPDF$$P50$$Gpubmedcentral$$H</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2816312/$$EHTML$$P50$$Gpubmedcentral$$H</linktohtml><link.rule.ids>230,314,727,780,784,885,27924,27925,41488,42557,51319,53791,53793</link.rule.ids></links><search><creatorcontrib>Wu, Hai-feng</creatorcontrib><creatorcontrib>Zhang, Pei-zhi</creatorcontrib><creatorcontrib>Wu, Jun</creatorcontrib><title>A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular SNAr sequence</title><title>Journal of Zhejiang University. B. Science</title><addtitle>J. Zhejiang Univ. Sci. B</addtitle><addtitle>Journal of Zhejiang University Science</addtitle><description>A novel tandem reductive amination/intermolecular nucleophilic aromatic substitution （SNAr） sequence has been established for the synthesis of amine containing pyrimidine in formation of one carbon-oxygen and one carbon-nitrogen bonds in a one-pot fashion. Treatment of aldehyde with arylamine, 2-methanesulfonyl-4,6-dimeth- oxypyrimidine and sodium borohydride provides good overall yield. The p-toluenesulfonic acid （PTSA） can be used as activator and is generally needed in the reaction. Dioxane is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran （THF）, MeCN, toluene and dichloromethane. The procedure is carried out effectively in the presence of K2CO3. The reaction proceeds smoothly with aromatic aldehydes and arylamines possessing electron-donating or -withdrawing groups. This method can be applied to the synthesis of the oilseed rape herbicide and is superior to the classical one in several aspects： cutting out several purification steps, minimizing solvent use and chemical waste, and saving time. Its advantages such as operational convenience, high-efficient synthesis, and starting material availability make it a desirable method for preparing amines with molecular diversity and biological activity.</description><subject>Aldehydes</subject><subject>Amines</subject><subject>Ar序列</subject><subject>Biological</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Biotechnology</subject><subject>Cutting</subject><subject>Derivatives</subject><subject>Sodium</subject><subject>Solvents</subject><subject>Synthesis</subject><subject>亲核取代反应</subject><subject>分子间</subject><subject>对甲苯磺酸</subject><subject>简便合成</subject><subject>衍生物</subject><subject>还原胺化</subject><issn>1673-1581</issn><issn>1862-1783</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp1kU2P0zAQhi0EYj_gyN3iwildf8RxfEEqK2CRVnAAztbUmbQuid21k2rLr8elBYkDp7FmnnnHMy8hrzhb8Ebym-3POS_eMcOYMPIJueRtIyquW_m0vBstK65afkGuct4yVtdMN8_JhWCc1U0tL0le0h6cH5DmQ5g2mH2msaeignQY4uNhd0h-9J0PSDtMfg-T32Omew8U6AShw5Em7GZ3zFMYfShEDDc-TJjGOKCbB0j06-dlohkfZgwOX5BnPQwZX57jNfn-4f2327vq_svHT7fL-8rVwkxV3TfYOe00Cil5J4RpwQBvVqo1rnda4EqrGhSXrAFnFHAlWmCKlRpnLcpr8vaku5tXY5HCMCUY7K5sVLazEbz9txL8xq7j3or2eFpRBN6cBVIsX8-THX12OAwQMM7ZGqaNrNVvsjqRLsWcE_Z_p3Bmj2L26JP941PhFyc-Fy6sMdltnFMo1_hvw-vzgE0M64fSY1fgfvTFOSul4EppLn8BZ3GjTw</recordid><startdate>20100201</startdate><enddate>20100201</enddate><creator>Wu, Hai-feng</creator><creator>Zhang, Pei-zhi</creator><creator>Wu, Jun</creator><general>SP Zhejiang University Press</general><general>Zhejiang University Press</general><scope>2RA</scope><scope>92L</scope><scope>CQIGP</scope><scope>W92</scope><scope>~WA</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SC</scope><scope>7SP</scope><scope>7SR</scope><scope>7TB</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>5PM</scope></search><sort><creationdate>20100201</creationdate><title>A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular SNAr sequence</title><author>Wu, Hai-feng ; Zhang, Pei-zhi ; Wu, Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-4f6edc7c7e2331d2298a9a16b589cfc72eb754a51306ac95a1528a050fc7108e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Aldehydes</topic><topic>Amines</topic><topic>Ar序列</topic><topic>Biological</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Biotechnology</topic><topic>Cutting</topic><topic>Derivatives</topic><topic>Sodium</topic><topic>Solvents</topic><topic>Synthesis</topic><topic>亲核取代反应</topic><topic>分子间</topic><topic>对甲苯磺酸</topic><topic>简便合成</topic><topic>衍生物</topic><topic>还原胺化</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Hai-feng</creatorcontrib><creatorcontrib>Zhang, Pei-zhi</creatorcontrib><creatorcontrib>Wu, Jun</creatorcontrib><collection>中文科技期刊数据库</collection><collection>中文科技期刊数据库-CALIS站点</collection><collection>中文科技期刊数据库-7.0平台</collection><collection>中文科技期刊数据库-工程技术</collection><collection>中文科技期刊数据库- 镜像站点</collection><collection>CrossRef</collection><collection>Computer and Information Systems Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of Zhejiang University. B. Science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Hai-feng</au><au>Zhang, Pei-zhi</au><au>Wu, Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular SNAr sequence</atitle><jtitle>Journal of Zhejiang University. B. Science</jtitle><stitle>J. Zhejiang Univ. Sci. B</stitle><addtitle>Journal of Zhejiang University Science</addtitle><date>2010-02-01</date><risdate>2010</risdate><volume>11</volume><issue>2</issue><spage>94</spage><epage>101</epage><pages>94-101</pages><issn>1673-1581</issn><eissn>1862-1783</eissn><abstract>A novel tandem reductive amination/intermolecular nucleophilic aromatic substitution （SNAr） sequence has been established for the synthesis of amine containing pyrimidine in formation of one carbon-oxygen and one carbon-nitrogen bonds in a one-pot fashion. Treatment of aldehyde with arylamine, 2-methanesulfonyl-4,6-dimeth- oxypyrimidine and sodium borohydride provides good overall yield. The p-toluenesulfonic acid （PTSA） can be used as activator and is generally needed in the reaction. Dioxane is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran （THF）, MeCN, toluene and dichloromethane. The procedure is carried out effectively in the presence of K2CO3. The reaction proceeds smoothly with aromatic aldehydes and arylamines possessing electron-donating or -withdrawing groups. This method can be applied to the synthesis of the oilseed rape herbicide and is superior to the classical one in several aspects： cutting out several purification steps, minimizing solvent use and chemical waste, and saving time. Its advantages such as operational convenience, high-efficient synthesis, and starting material availability make it a desirable method for preparing amines with molecular diversity and biological activity.</abstract><cop>Heidelberg</cop><pub>SP Zhejiang University Press</pub><pmid>20104643</pmid><doi>10.1631/jzus.B0900293</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Aldehydes Amines Ar序列 Biological Biomedical and Life Sciences Biomedicine Biotechnology Cutting Derivatives Sodium Solvents Synthesis 亲核取代反应 分子间 对甲苯磺酸 简便合成 衍生物 还原胺化 |
| title | A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular SNAr sequence |
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