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2nd April 2013 @ 02:13
Mnr: MNR91-100

Starting material - Synthesis of thienopyrimidine MNR89-3

As for Chlorination of MNR89 To Give MNR99-2

 

Hazard Assessment

HIRAC MNR99.pdf

Procedure


Reaction carried out in two lots due to scale and volume of POCl3 required.

A

To MNR89-3 (3.95 g, 25.96 mmol) at room temperature was added POCl3 (24 mL, 259 mmol) under argon and the mixture was heated to reflux for 2 hours during which time the reaction turned a dark brown colour.  The the reaction was then allowed to reach room temperature and was slowly added dropwise to ice ice (400 mL) in a large beaker.  The mixture was then slowly neutralised with sodium bicarbonate.  A pale brown solid also began to precipitate out during the quencing.  Once the reaction was fully quenched it was extracted with EtOAc (400 mL x 2), the organics were combined and washed with brine (100 mL) then dried with anhydrous magnesium sulfate, filtered and concentrated to give a pale orange solid.

B as above and quenched in the same ice bath, starting material (4.10 g, 26.9 mmol)

Column 40-80% EtOAc/Hex

Fracs 1-5 - 8.269 g, 48.5 mmol, 92% as a white crystaline solid

NMR

 

mnr99-3_frac1-5_1H.pdf
mnr99-3_frac1-5.zip

Conclusion

Clean porduct in good high yield.

Strings

Starting material

InChI=1S/C6H4N2OS/c9-6-5-4(1-2-10-5)7-3-8-6/h1-3H,(H,7,8,9)

Product

InChI=1S/C6H3ClN2S/c7-6-5-4(1-2-10-5)8-3-9-6/h1-3H

 

 

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Attached Files
mnr99-3_frac1-5_1H.pdf
mnr99-3_frac1-5.zip