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25th November 2014 @ 13:24
Summary: For this synthesis I modified the amine portion of the thienopyrimidine building block by reacting the brominated precursor (PT-19, ~600mg remaining) with ethanolamine. The product of this reaction was then cross-coupled with the sulfonamide (PT-1-18) in TF7-1.   Hazard and Risk Assessment: [data]14209[/data] Reaction Scheme: Procedure: The procedure used was analogous to the one already performed by Alice Williamson (AEW57-2).6-bromo-4-chlorothieno[3,2-d]pyrimidine (75mg, 0.44mmol, 1 equiv) and ethanolamine (2.66 mL, 4.40mmol, 10 equiv) were stirred together at 100C for 1 hour. The solid product was filtered through with water and collected to give a yield of 46mg (0.168mmol, 38.1%). NMR spectra indicated the crude yield was sufficiently pure to be taken on as-is, as the thienopyrimidine starting material had been fully consumed in the reaction, and any residual amine was removed when the solid was filtered with water.  Data: [data]14217[/data][data]14231[/data][data]14345[/data][data]14571[/data][data]14573[/data][data]14677[/data] InChi: InChI=1S/C8H7BrN2OS/c9-7-3-6-8(13-7)5(1-2-12)10-4-11-6/h3-4,12H,1-2H2  
Attached Files
RA TF5-1.doc
TF5-1 1H & 13C DMSO Raw.tar
TF5-1 1H, 13C, D90, D135 DMSO Raw.tar
TF5-1 Nominal Mass Spec.jpg
TF5-1 Synthesis.png
TF5-1 High Res MS.jpg