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2nd July 2014 @ 19:11
    The procedure was used from [blog=7748]Synthesis of 3-(4-(2-(dimethylamino)ethoxy)thieno[3,2-d]pyrimidin-6-yl)benzenesulfonamide (MJT 18-1)[/blog].   PT-21-B1 (28.3 mg, 0.1 mmol) was dissolved in isopropyl alcohol (2 mL) and to this was added PT-20-3-C1 (47 mg, 0.12 mmol, 1.2 eq) followed by potassium carbonate solution (1M, 0.2 mL, 2 equivalents). The solution was degassed with nitrogen for 5 minutes and Pd(dppf)2.CH2Cl2 (16 mg, 20 umol, 20 mol%) was added. The reaction was heated to 90°C for 30 minutes under microwave irradiation in a sealed vessel, then dry-loaded onto silica and purified using dry column vacuum chromatography (0-10% methanol in chloroform, 20 fractions, then 1% sat. aq. ammonia, 9% methanol, 90% chloroform for 5 tubes) to give the title compound as the most beautiful tan solid I've ever seen (16.8 mg, 52 umol, 52%), which was only sparingly soluble in chloroform.  NMR: Consistent with desired product. (Note: earlier data was taken when spectrometer was accidentally set to +45°C by a previous user, and is present in the tarball) [data]12307[/data] Mass Spectroscopy (Nominal): Consistent. [M+H] and [2M+H] visible. [data]12271[/data] Mass Spectroscopy (Accurate): Main peak consistent to within 2ppm: Observed: 321.0474 Calculated: 321.04801 13C peak consistent to within 4ppm: Observed: 322.0499 Calculated: 322.05137 13C * 2 peak consistent to within 3ppm: Observed: 323.0447 Calculated: 323.04381 [data]12325[/data][data]12341[/data]
Attached Files
CJCOSDD_ptm22c1meod_020714_1H-13C_pr500.tar
PT-22.png
PT-22-C1 ESI Nominal.jpg
NMR-Combined.png
CJCOSDD_ptm22c1meodlong_030714_1H-1H-13C_av600_JulIV-00083.tar
1H 13C interpreted.pdf
PT-22-C1 ESI Accurate.jpg
IMG_20140707_115156.jpg