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26th November 2014 @ 12:41
Summary: For this synthesis I modified the amine portion of the thienopyrimidine building block by reacting the brominated precursor (PT-19, ~600mg already in stock) with 3-aminopropan-1-ol. The product of this reaction was then cross-coupled with the sulfonamide (PT-1-18) in TF8-1. Hazard and Risk Assessment: [data]14215[/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 3-aminopropan-1-ol (3.35 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 57.3mg (0.199mmol, 45.2%). 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]14219[/data][data]14227[/data][data]14347[/data][data]14575[/data][data]14577[/data][data]14679[/data] InChi: InChI=1S/C6H2BrClN2S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H
Attached Files
RA TF6-1.doc
TF6-1 1H & 13C DMSO Raw.tar
TF6-1 1H, 13C, D90, D135 DMSO Raw.tar
TF6-1 Nominal Mass Spec.jpg
TF6-1 Synthesis.png
TF6-1 High Res MS.jpg