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OpenSourceMalaria / OSM_To_Do_List

Action Items in the Open Source Malaria Consortium
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Synthesis of 4-chloro-6-(3-(pyridin-2-yl)phenyl)thieno[3,2-d]pyrimidine #117

Closed pluralise closed 10 years ago

pluralise commented 10 years ago

osm target nov dec 2013

I'm currently attempting to synthesise this aminothienopyrimidine (series 2) analogue.

alintheopen commented 10 years ago

Hi Matt, Thanks for this could you possibly draw out the scheme and post to GitHub? Cheers Alice

On Fri, Dec 20, 2013 at 11:41 AM, MJTarnowski notifications@github.comwrote:

To date I've deprotonated 4-chlorothieno [3,2-d] pyrimidine at the 7-position, iodinated and coupled this with TMS acetylene (sonogashira). Deprotection gives a terminal alkyne at the 7-position of the starting material

Next, using Crépin, D. and Harrity, J. P. A. H., Organic Letters (2013), 15, 4222, (DOI: 10.1021/ol401952k) we hope to get the compound that is the subject of this GitHub post via cycloaddition with 6-(pyridin-2-yl)-2H-pyran-2-one. Then substitution of the chlorine in 4-position with an amine. If this goes as planned we'll use other pyrones and amines to give some aminothienopyrimidine analogues.

After the cycloaddition it should be possible to iodinate at the ortho position of the newly formed benzene ring using the metal-aluminium bond in the product, could this give some analogues to probe the solubility issues discussed in the May consultation ( http://malaria.ourexperiment.org/osdd_malaria_shared/7509/post.html)? Though perhaps due to the lack of the sulfonamide group it's not appropriate to target these compounds?

— Reply to this email directly or view it on GitHubhttps://github.com/OpenSourceMalaria/OSM_To_Do_List/issues/117#issuecomment-30980700 .

mattodd commented 10 years ago

Hi @MJTarnowski - it's been a while! Do we close out this item, or did you make the molecule?

pluralise commented 10 years ago

Hi @mattodd, we should close the item as unfortunately I was not able to make the molecule.

mattodd commented 10 years ago

No problem. Note added to the wiki to ensure this is not orphaned

http://openwetware.org/wiki/OpenSourceMalaria:GSK_Amino-thienopyrimidine_Series#Organic_Synthesis

Closing.