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14th October 2014 @ 13:02

Summary:

Cross-coupling of the product from TF2-1 to form TF3-1 (Compound 24 in the Series 3 lab book) The chemistry of this reaction is analogous to PT-22, synthesised by Patrick.

Hazard and Risk Assessment:

RA TF3-1.doc

Reaction Scheme:

 

Procedure:

The combination of the two above building blocks to form compound 24 is analogous to this synthesis alredy performed by Patrick. 

6-bromo-7-methylthieno[3,2-d]pyrimidin-4-amine [TF2] (84.9 mg, 0.3 mmol), MNR103 (141 mg, 0.36 mmol), and Pd(dppf)Cl2 (48 mg, 60 μmol, 20 mol%) were dissolved in isopropyl alcohol (6 mL). Potassium carbonate solution (1M, 0.6 mL) was added.

The reaction was heated to 90°C for 30 minutes under microwave irradiation in a sealed vessel.

The product was then purified using column chromatography (0-5% methanol in chloroform for 10 tubes, 5% methanol in chloroform for 20 tubes, 10% methanol in chloroform for 10 tubes) and evaporated to dryness to give a pale brown solid (54.2mg, 0.169mmol, 56.3%). The solid was completely insoluble in chloroform and soluble in methanol.

Data:

TF3-1 Final Product in Methanol-d4.tar
TF3-1 Final Product DEPT90 MeOD.pdf
TF3-1 Final Product 13C MeOD.pdf
TF3-1 Final Product DEPT135 MeOD.pdf
TF3-1 Final Product 1H MeOD.pdf
TF3-1 Nominal Mass Spec (Crude).jpg
TF3-1 Nominal Mass Spec (Crude) Zoomed.jpg
TF3-1 Accurate Mass Spec.jpg
TF3-1.png
TF3-1 Synthesis.png

InChi:

InChI=1S/C13H12N4O2S2/c1-7-10-12(13(14)17-6-16-10)20-11(7)8-3-2-4-9(5-8)21(15,18)19/h2-6H,1H3,(H2,14,16,17)(H2,15,18,19)

Attached Files
RA TF3-1.doc
TF3-1 Final Product in Methanol-d4.tar
TF3-1 Final Product DEPT90 MeOD.pdf
TF3-1 Final Product 13C MeOD.pdf
TF3-1 Final Product DEPT135 MeOD.pdf
TF3-1 Final Product 1H MeOD.pdf
TF3-1 Nominal Mass Spec (Crude).jpg
TF3-1 Nominal Mass Spec (Crude) Zoomed.jpg
TF3-1 Accurate Mass Spec.jpg
TF3-1.png
TF3-1 Synthesis.png