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26th June 2013 @ 02:44

Bromination of MJT 7-1This is an effort towards synthesising aminothienopyrimidine analogues discussed in the May 2013 Open Consultation.

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Reaction gave mixed products and lots of SM remained unreacted. Crude product was discarded since TLC showed it had degraded. SM was not recovered; reaction was repeated in MJT 9-2.

 

 

 

Procedure

MJT 7-1 (0.2377 g, 1.44 mmol, 1 equiv.) was dissolved in THF (29 mL) and cooled to -78 °C.  To the stirring solution was added n-BuLi (2.5 M in hexane, 0.86 mL, 2.16 mmol, 1.5 equiv.) and the stirring was continued for 30 minutes.  Bromine (0.14 mL, 2.88 mmol, 2 equiv.) was added dropwise and the reaction mixture was allowed to reach room temperature and was stirred for 2.5 hours. The reaction is an orange solution and TLC shows the reaction is not completed. The reaction was left to stir for 1.5h more before sodium thiosulfate solution (30 mL) was added, an aqueous and an organic layer formed. The crude product was collected by washing with ethyl acetate (30 mL) x 3. The organic layer was washed with brine (20 mL), dried with Na2SO4 and solvent removed to give MJT 9-1 (0.175 g, 0.717 mmol, 50 %) as an orange oil.

Hazard and Risk Assessment


HIRAC MJT 9-1.pdf

Analysis


TLC 2.5h, 30% and 50% hexane in ethyl acetate

TLC MJT 9-1.JPG

1H NMR

MJT_9-1_crude.pdf
 
MJT 9-1 crude H NMR raw data

MJT_9-1_crude_degraded.pdf
 
MJT 9-1 degraded crude product H NMR raw data
Linked Posts
Attached Files
MJT 9-1 reaction scheme.png
HIRAC MJT 9-1.pdf
MJT 9-1 data table.PNG
TLC MJT 9-1.JPG
MJT 9-2 amoun ts table.PNG
MJT_9-1_crude.pdf
MJT_9-1_crude_degraded.pdf
MJT 9-1 crude H NMR raw data
MJT 9-1 degraded crude product H NMR raw data