Development of Scalable Synthesis of 5-Butyl-4-(4-methoxyphenyl)-6-phenylpyrimidin-2-amine (WQE-134), a Dual Inhibitor of Nitric Oxide and Prostaglandin E2 Production
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00533528" target="_blank" >RIV/61388963:_____/20:00533528 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1021/acs.oprd.0c00324" target="_blank" >https://doi.org/10.1021/acs.oprd.0c00324</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.oprd.0c00324" target="_blank" >10.1021/acs.oprd.0c00324</a>
Alternative languages
Result language
angličtina
Original language name
Development of Scalable Synthesis of 5-Butyl-4-(4-methoxyphenyl)-6-phenylpyrimidin-2-amine (WQE-134), a Dual Inhibitor of Nitric Oxide and Prostaglandin E2 Production
Original language description
We report a scalable efficient synthesis of 5-butyl-4-(4-methoxyphenyl)-6-phenylpyrimidin-2-amine (WQE-134), a dual inhibitor of nitric oxide and prostaglandin E2 production with potent anti-inflammatory properties. The original five-step synthesis (40% overall yield) was based on two Suzuki–Miyaura reactions and required chromatographic purification of both the intermediate and final products. The novel synthetic pathway is based on cyclization of 2-butyl-1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione with guanidinium methanesulfonate using Eaton’s reagent (P2O5/MsOH) at 50 °C. The two-step synthesis (34% overall yield) can be performed on a multigram to kilogram scale, and purification of the final product consists of simple extraction (dichloromethane) and crystallization (ethyl acetate and methanol).
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/TE01020028" target="_blank" >TE01020028: Center for Development of Original Drugs</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic Process Research & Development
ISSN
1083-6160
e-ISSN
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Volume of the periodical
24
Issue of the periodical within the volume
9
Country of publishing house
US - UNITED STATES
Number of pages
7
Pages from-to
1718-1724
UT code for WoS article
000574921200016
EID of the result in the Scopus database
2-s2.0-85093120269