CN(C)/[CH:3]=[CH:4]/[C:5]1[C:10]([C:11]#[N:12])=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[N:8]=[C:7]([S:21][CH3:22])[N:6]=1.[BrH:24]>C(O)(=O)C>[Br:24][C:11]1[C:10]2[C:9]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=3)=[N:8][C:7]([S:21][CH3:22])=[N:6][C:5]=2[CH:4]=[CH:3][N:12]=1.[BrH:24]The crude 4-[(E)-2-(dimethylamino)ethenyl]-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrile (1.47 g) was dissolved into acetic acid (5 mL) and a solution of 33% HBr in glacial acetic acid (10 mL) was added. The reaction mixture was stirred at room temperature for 20 min. The mixture was then concentrated under reduced pressure to give the bromopyridine as a HBr salt.
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