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26th June 2013 @ 06:38

Bromination of MJT 8-1This is an effort towards synthesising aminothienopyrimidine analogues discussed in the May 2013 Open Consultation.

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Product was synthesised in 57 % yield. and taken forward in a suzuki coupling with MNR 103 - see MJT 17-1.

This is a novel compound; data to be collected: IR, LRMS, HRMS

 

 

 

 



Procedure

MJT 8-1 (0.2386 g, 1.33 mmol, 1 equiv.) was dissolved in THF (27 mL) and cooled to -78 °C.  To the stirring solution was added n-BuLi (2.5 M in hexane, 0.80 mL, 2.00 mmol, 1.5 equiv.) and the stirring was continued for 30 minutes.  Bromine (0.14 mL, 2.66 mmol, 2 equiv.) was added dropwise and the reaction mixture was allowed to reach room temperature and was stirred for 2.5 hours, it is now an orange solution. TLC analysis showed reaction did not go to completion. The reaction was stirred for 1h more, then saturated sodium thiosulfate solution (30 mL) was added - a precipitate formed. The resulting solution was washed with ethyl acetate (30 mL) x 3. The organic layer was collected and washed with brine (20 mL) in to which the precipitate dissolved, then dried with Na2SO4 and concentrated to an orange solid (0.394 g, >100 %). Column chromatography (50 % hexanes / ethyl acetate) was used to isolate the product (0.1934 g, 0.75 mmol, 57 %) as a white solid.

Hazard and Risk Assessment

HIRAC MJT 10-1.pdf

Analysis

TLC 2.5h, 50% hexane / ethyl acetate

MJT 10-1 TLC.JPG

Characterisation Data

1H NMR

MJT_10-1_H.pdf
 
MJT 10-1 H NMR raw data

13C NMR

MJT_10-1_Carbon.pdf
 
MJT 10-1 carbon NMR raw data

Mpt. 123-124 ˚C

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Attached Files
HIRAC MJT 10-1.pdf
HIRAC MJT 10-1
amounts table MJT 10-1.PNG
MJT 10-1 TLC.JPG
MJT_10-1_H.pdf
MJT_10-1_Carbon.pdf
MJT 10-1 carbon NMR raw data
MJT 10-1 H NMR raw data