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2nd May 2013 @ 08:19
Mnr: mnr121-130

Starting material from commercially purchased 4-chloroethieno[3,2-d]pyrimidine

As for Nucleophilic Displacement of MNR99 with Morpholine to give MNR100-1 and Nucleophilic Displacement of MNR99 with Dimethylamine to give MNR122-1



Hazard Assessment


To 4-chloroethieno[3,2-d]pyrimidine (1.0 g, 5.86 mmol) in THF (7 mL) (ethanol (5 mL added to get the starting material into solution) was added 1-methylpiperazine (1.3 mL, 11.72 mmol at 0 C.  Stirring was contiued for 6 hours.  HCl (1M) (10 mL) was added and extracted with EtOAC (20 mL x 3).  The organic fractions were combined, dried, filtered and concentrated to yeild 20 mg of and orange oil that slowly solidifed on standing.  

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Thinking that there was a solubiltiy probelm with the product the aqueous layer was concentrated to give a yellow solid.  1H NMR of this showed product and the excess piperazine.  Attempts to recrystalise this in Methonal/Hexane gave a white sold but most of this was lost on washing.  NMR showed clean product although it was thought this was the HCl.  All the material was then washed with sodium hydrogen carbonate solution (30 mL) and extraced with EtOAc (40 ml x 3).  The organic fractions were combined, dried, filtered and concentrated to yeild (1.186 g, 5.06 mmol, 86%) as a pale yellow solid. 



- 1H NMR aqueous layer

- 1H NMR recrystallisationof the HCl salt

- 1H NMR or organic layer after making pH12


If repeating this reaction the reaction mixture should just be washed with sodium hydrogen carbonate solution and extracted.  Probelms arrose by making the HCl salt by mistake.


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