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20th October 2014 @ 08:50

Summary:

Cross-coupling of the product from TF2-1 and the leftover product from PT-1-20-2 .The procedure used was analogous to that of TF3-1 and PT-22.

Hazard and Risk Assessment:

RA TF4-1.doc

Reaction Scheme:

Procedure:

The procedure was analogous to the syntheses of TF3-1 and PT-22, using the methylated boronic acid pinocol ester instead (which was fortunately in stock).

6-bromo-7-methylthieno[3,2-d]pyrimidin-4-amine [TF2] (17.05 mg, 0.070 mmol, 1 eq), methylated MNR-103 (28.3 mg, 0.078 mmol, 1.2 eq) and Pd(dppf)Cl2 (9.64 mg, 20mol%) were dissolved in isopropyl alcohol (1.2 mL). Potassium carbonate solution (1M, 0.36 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 (0-10% methanol in chloroform for 20 tubes) and evaporated to dryness to give a yield of 20.0mg (0.060 mmol, 85.7%) of pale brown product. The solid was soluble in methanol, moreso than the previous product (TF3-1).

Data:

TF4-1 1H MeOD Crude.pdf
TF4-1 1H MeOD.pdf
TF4-1 13C MeOD.pdf
TF4-1 COSY MeOD.pdf
TF4-1 HMBC MeOD.pdf
TF4-1 HSQC MeOD.pdf
TF4-1 DEPT-135 MeOD.pdf
TF4-1 NOESY MeOD.pdf
TF4-1 Raw.tar
TF4-1 Accurate Mass Spec.jpg
TF4-1 Nominal Mass Spec Zoomed.jpg
TF4-1 Nominal Mass Spec.jpg
TF4-1.png
TF4-1 Synthesis.png

InChi:

InChI=1S/C14H14N4O2S2/c1-7-3-4-9(22(16,19)20)5-10(7)12-8(2)11-13(21-12)14(15)18-6-17-11/h3-6H,1-2H3,(H2,15,17,18)(H2,16,19,20)

Attached Files
Compound 25.png
Compound 25 Synthesis.png
RA TF4-1.doc
TF4-1 1H MeOD Crude.pdf
TF4-1 1H MeOD.pdf
TF4-1 13C MeOD.pdf
TF4-1 COSY MeOD.pdf
TF4-1 HMBC MeOD.pdf
TF4-1 HSQC MeOD.pdf
TF4-1 DEPT-135 MeOD.pdf
TF4-1 NOESY MeOD.pdf
TF4-1 Raw.tar
TF4-1 Accurate Mass Spec.jpg
TF4-1 Nominal Mass Spec Zoomed.jpg
TF4-1 Nominal Mass Spec.jpg
TF4-1.png
TF4-1 Synthesis.png