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28th January 2015 @ 11:58

Summary

This is the third synthesis in a series of three amino-thienoyprimidine compounds with a modification to the sulfonamide group on the right-hand portion of the molecule. The sulfonamide in this target is substituted with the dimethylamine group.

Hazard and Risk Assessment:

RA TF18-1.doc

Reaction Scheme:

Procedure:

The procedure used is analogous to Patrick's synthesis, PT-22, and my previous syntheses: TF3-1TF4-1TF7-1 and TF8-1.

Two equivalents of the sulfonamide from the previous step, TF14-1, were used in order to adjust for the ~50% purity.

N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide [TF14-1] (47.0 mg, 0.139 mmol, 2 equiv), 6-bromothieno[3,2-d]pyrimidin-4-amine [TF15-1] (17.5 mg, 0.0761 mol, 1 equiv) and Pd2Cl2(dppf) (12.2 mg, 20 mol%) were dissolved in isopropanol (1.5 mL), and potassium carbonate solution (1M, 0.15 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 27.3 mg (0.0816 mmol, 58.7 %) of pale brown solid.

Data:

TF18-1 Synthesis.png
TF18-1.png
TF18-1 Low Res MS.jpg
TF18-1 1H & 13C DMSO.zip
TF18-1 High Res MS.jpg

InChi:

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

Attached Files
TF18-1 Synthesis.png
TF18-1.png
RA TF18-1.doc
TF18-1 1H & 13C DMSO.zip
TF18-1 Low Res MS.jpg
TF18-1 High Res MS.jpg