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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


Procedure

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.  

2013-05-03 11.22.17.jpg

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. 

NMR

 

mnr125-1_aq_1H.pdf
- 1H NMR aqueous layer

mnr125-1_aq_recrystal1_1H.pdf
- 1H NMR recrystallisationof the HCl salt

mnr125-1_pH12_1H.pdf
mnr126-1_pH12.zip
- 1H NMR or organic layer after making pH12

Conclusion

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.

 

Linked Posts
Attached Files
MNR125-1_table.PNG
MNR125_scheme.png
mnr125-1_pH12_1H.pdf
mnr125-1_aq_1H.pdf
mnr125-1_aq_recrystal1_1H.pdf
2013-05-03 11.22.17.jpg
mnr126-1_pH12.zip