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1st December 2014 @ 11:51

Summary:

Suzuki cross-coupling on the product of TF5-1. The reaction is analogous to previous cross-couplings performed by Patrick (PT-22), and my own syntheses, TF3-1 and TF4-1.

 

Hazard and Risk Assessment:

RA TF7-1.doc

Reaction Scheme:



Procedure:

The procedure was scaled down from analogous syntheses so as to use 20mg of the thienopyrimidine starting material.
 
TF5-1 (20mg, 0.073mmol), MNR103 (24.8mg, 0.0876mmol) and PdCl2(dppf) (11.92mg, 20mol%) were placed in a sealed vessel along with IPA (1.5mL) and K2CO3 (0.15mL). The vessel was heated in a 200W microwave at 90oC for 30 mins.
 
The reaction mixture was separated dry flash chromatography to give a 12.1mg yield (0.0345mmol, 47.3%) of pale brown solid.
 
 
Data:
 
TF7-1 1H & 13C DMSO.tar
TF7-1 Nominal Mass Spec.jpg
TF7-1 Synthesis.png
TF7-1.png
TF7-1 High Res MS.jpg
 
InChi:
 
InChI=1S/C14H14N4O3S2/c15-23(20,21)10-3-1-2-9(6-10)12-7-11-13(22-12)14(16-4-5-19)18-8-17-11/h1-3,6-8,19H,4-5H2,(H2,15,20,21)(H,16,17,18)
 
 
Attached Files
1st December 2014 @ 11:05

Summary:

Suzuki cross-coupling on the product of TF6-1. The reaction is analogous to previous cross-couplings performed by Patrick (PT-22), and my own syntheses, TF3-1 and TF4-1.

 

Hazard and Risk Assessment:

RA TF8-1.doc

Reaction Scheme:



Procedure:

The procedure was scaled down from analogous syntheses so as to use 20mg of the thienopyrimidine starting material.

TF6-1 (20mg, 0.069mmol), MNR103 (23.4mg, 0.0828mmol) and PdCl2(dppf) (11.26mg, 20mol%) were placed in a sealed vessel along with IPA (1.5mL) and K2CO3 (0.15mL). The vessel was heated in a 200W microwave at 90oC for 30 mins.

The reaction mixture was purified to give a rich brown solid with a yield of 17.8mg (0.0488mmol, 70.8%). 

Data:
 
TF8-1 1H & 13C DMSO.tar
TF8-1 Nominal Mass Spec.jpg
TF8-1.png
TF8-1 Synthesis.png
TF8-1 High Res MS.jpg
 
InChi:
 
InChI=1S/C15H16N4O3S2/c16-24(21,22)11-4-1-3-10(7-11)13-8-12-14(23-13)15(19-9-18-12)17-5-2-6-20/h1,3-4,7-9,20H,2,5-6H2,(H2,16,21,22)(H,17,18,19)
 
Attached Files