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22nd July 2013 @ 07:41
 Coupling of MJT 16-1 with ortho-sulfonamide boronic acid ester, MNR 103-1. Following methods used by Althea: 90oC for 30 minutes in a microwave reactor (200 W). This is the final stage of the synthesis of one of the aminothienopyrimidine analogues decided upon in the May 2013 Open Consultation. *** MJT 18-1 was synthesised in 56 % yield. This is a novel compound; data to be collected: IR, Mpt, LRMS, HRMS Procedure  A solution of MJT 16-1 (29.5 mg, 0.0976 mmol, 1 equiv.), MNR 103-1 (34.0 mg,  0.119 mmol, 1.2 equiv.) and PdCl2dppf (27.0 mg, 0.0199 mmol, 0.20 equiv.) in isopropanol (2.0 mL) and K2CO3 (1 M,  0.20 mL, 0.20 mmol, 2.0 equiv.) was degassed with argon for 10 minutes. The reaction mixture was heated at 90oC for 30 minutes in a microwave reactor (200 W). It is now a black solution. The reaction mixture was diluted with MeOH (50 mL) and filtered through celite. The resulting solution was concentrated to a black solid (0.090 g, >100 %). TLC showed no SM remained and several new products had formed. Column chromatography (2.5 % MeOH, 0.5 % NH3, 97 % DCM) was used to purify the product and gave one pure fraction as a brown solid (0.021 g, 0.055 mmol, 56 %). Hazard and Risk Assessment [data]6992[/data] Data TLC [data]7062[/data] Characterisation Data 1H NMR [data]7216[/data][data]7224[/data] 13C NMR [data]7218[/data][data]7220[/data]
Attached Files
Reaction Scheme MJT 18-1.png
HIRAC MJT 18-1.pdf
TLC MJT 18-1 crude
Amounts table MJT 18-1.PNG
MJT 18-1 proton.pdf
MJT 18-1 carbon.pdf
MJT 18-1 C NMR raw data
MJT 18-1 H NMR raw data