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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:
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:
InChi:
InChI=1S/C6H2BrClN2S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H
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:
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:
InChi:
InChI=1S/C8H7BrN2OS/c9-7-3-6-8(13-7)5(1-2-12)10-4-11-6/h3-4,12H,1-2H2