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20th May 2013 @ 05:09
Reaction returned SM - mono-methyl derivative will be synthesised from MNR 99-3 and methyl amine prior to bromination Starting material from [blog=7264]Amination of chlorobromothienopyrimidine (AT-6-5)[/blog] Procedure: A solution of acetic anhydride (49 microL, 0.52 mmol, 1.2 equiv.) in dry CH2Cl2 (0.5 mL) was added dropwise over 15 min to a  stirred solution of AT 6-5 (100 mg, 0.43 mmol, 1.0 equiv.) and triethylamine (73 microL, 0.52 mmol, 1.2 equiv.) in dry CH2Cl2 (6.5 mL). After 15 minutes and then 1 h TLC analysis seemed to suggest no reaction but the SM and reaction mixture contained a streak to the main spot that is not present in the product spot. Decided to leave stirring o/n will check in the morning. Volatiles removed in vacuo and the off white powder was sonicated and water and the cream solid filtered off to give 67 mg of SM. Expected more product so: The aqueous layer was extracted with ethyl acetate, washed with water, brine, dried (MgSO4), filtered and evaporated to give starting material (20 mg).  Decided on alternative method for synthesis of mono-methylated analog.   Hazard and Risk Assessment: [data]6444[/data] Literature Ref: InChi InChI=1S/C6H4BrN3S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H,(H2,8,9,10) to InChI=1S/C8H6BrN3OS/c1-4(13)12-8-7-5(10-3-11-8)2-6(9)14-7/h2-3H,1H3,(H,10,11,12,13)
Attached Files
AEW 56-1.png
HIRAC AEW 56-1.pdf