All Notebooks | Help | Support | About
20th January 2014 @ 04:26
Reaction successful, product obtained with a yield of 33% Repeat of Althea's procedure AT-6-4 on a shorter time scale to optimise the amination reaction, as yield/products were found to be inconsistent (AEW 100-4). Reaction scheme Procedure AEW 99-1 (0.100 g, 0.4 mmol), isopropanol (3 mL) and ammonia (6 mL) were added to a sealed tube, stirred and heated at 120°C for 4 hours. The solvent was removed under vacuum. The crude product was purified by flash column chromatograph on silica (95:4.5:0.5 DCM:MeOH:NH3) to yield the product as a yellow solid (30 mg, 33%) Data -TLC TLC of crude reaction mixture in 95:45:0.5 DCM/MeOH/NH3. Not very clear separation, but solvent system used successfully to purify product (see AT-6-4) -NMR 1H NMR of starting material AEW 99-1 [data]8655[/data] 1H NMR of crude reaction mixture after drying. Starting material has disappeared, with a mix of other compounds. The major product appears to be the desired product upon comparison with AT 6-4.  [data]8657[/data] 1H NMR of first fraction after column purification. Appears to be a mix of products, with the major peaks not corresponding to the desired product. [data]8697[/data] 1H NMR of second fraction after column purification. One product, consistent with desired product according. [data]8695[/data] HIRAC [data]8533[/data] InChI InChI=1S/C6H2BrClN2S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H to InChI=1S/C6H4BrN3S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H,(H2,8,9,10)
Attached Files
CT 3-1 scheme.cdx
CT 3-1 scheme.png
CT 3-1 HIRAC.doc
CT 3-1 HIRAC.pdf
AEW 99-1 SM for CT 3-1 proton.pdf
CT 3-1 crude proton.pdf
AEW 99-1 SM for CT 3-1 proton.zip
CT 3-1 crude proton.zip
CT 3-1 column 0-7.JPG
CT 3-1 column 7-14.JPG
CT 3-1 column 14-22.JPG
CT 3-1 2nd fraction proton.pdf
CT 3-1 1st fraction proton.pdf
CT 3-1 1st fraction.zip
CT 3-1 2nd fraction.zip
CT 3-1 crude.JPG
Comments
Re: Synthesis of 6-Bromothieno[3,2-d]pyrimidin-4-amine (CT 3-1) by Alice Williamson
20th January 2014 @ 23:01
HIRAC approved. Discussed the use of a blast shield and the importance of ensuring that the reaction vessel and mixture has cooled down prior to opening the vessel.
Re: Synthesis of 6-Bromothieno[3,2-d]pyrimidin-4-amine (CT 3-1) by Matthew Todd
27th January 2014 @ 09:51
In your current write-up you don't talk about what the TLC of the crude told you, and therefore how you knew that the column was worth doing, and also which solvent system to use.

So what was your yield? Good reaction?

I don't think this compound has an OSM number - we'll assign one if not. http://malaria.ourexperiment.org/osm_procedures/group/Compound%20List