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10th December 2012 @ 05:29
This reaction is a repeat of JRC 32-2, and JRC 32-1, albeit using a microwave reactor and a bromine at the 6-position instead of an iodine. 4-(6-Bromothieno[3,2-d]pyrimidin-4-yl)morpholine (112.3 mg, 0.374 mmol, 1 eq.), 3-sulfamoylbenzene boronic acid, pinacol ester (37.7 mg, 0.13 mmol, 0.34 eq.) and AcOK (44 mg, 0.448 mmol, 1.1 eq.) were dissolved in 3 mL dioxane/H2O (degassed with argon). To this solution was added PdCl2(dtbpf) (6.3 mg, 0.11 mmol, 2.4 mol %). The solution was heated and stirred in a microwave reactor for 15 min at 150 °C at 150W. The solution was allowed to cool to rt. NOTE: INCORRECT QUANTITIES USED. TLC shows some starting material remaining, and several new products formed - all within a narrow rf band (0.3-0.4 in 10% MeOH/DCM). Crude reaction mixture purified via flash chromatography using DCM -> 10% MeOH/DCM as the eluent. Four pure fractions collected, though most mass remains in unisolated, non-pure fractions. F1: 1% MeOH/DCM [data]4411[/data] F2: 2% MeOH/DCM [data]4413[/data] F3: 5% MeOH/DCM [data]4415[/data] F4: 10% MeOH/DCM [data]4417[/data] None of these fractions containes the desired product by NMR. This is confusing because F3, by mass spec, showed a minor peak corresponding to the desired product:
Attached Files
JRC32-3.PNG
32-3F1.pdf
32-3f2.pdf
32-3F3.pdf
32-3F4.pdf