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10th March 2013 @ 22:25
Mnr: MNR101-110

Starting material from JRC58-1 and JRC58-2 (no lab book report).  These were combined and comlumed to purify the sstarting material.  Column was not a great success due to the poor solubility of the product.  Further attempts at a better crystalisation method should be looked into for future attempts.  Synthesis of 4-thiomorpholinothieno[3,2-d]pyrimidine (JRC 58-1)

As for Bromination of MNR100-2 to give MNR101-2

Hazard Assessment

HIRAC MNR101-1.pdf

Procedure

JRC58  (0.04 g, 0.17 mmol) was dissolved in THF (4 mL) (very poor solublity, majority did not go into the solution) and cooled to -78 °C.  To the stirring solution was added n-BuLi (2.5 M in hexanes, 0.1 mL, 0.25 mmol) and the stirring was continued for 30 minutes.  Bromine (0.02 mL, 0.34 mmol) was added dropwise and the reaction mixture was allowed to reach room temperature and was stirred for 2 hours.  Sodium thiosulfate solution (30 mL) was added and the mixture was extracted with EtOAc (3 x 10 mL).  The organic layers were commbined, dried and filteres then concentrated in vacuo to yield the crude.

TLC

SANY0067.JPG
100% EtOAc - SM spot from an old NMR sample

Column 

50-100% EtOAc - major sport came out too quickly

Fracs 

1-5

NMR

 
 
Conclusion

 

Strings

 Starting material

InChI=1S/C10H11N3S2/c1-4-15-9-8(1)11-7-12-10(9)13-2-5-14-6-3-13/h1,4,7H,2-3,5-6H2

Product

InChI=1S/C10H10BrN3S2/c11-8-5-7-9(16-8)10(13-6-12-7)14-1-3-15-4-2-14/h5-6H,1-4H2

Attached Files
MNR105_scheme.png
MNR105-1_table.PNG
SANY0067.JPG