2-Bromoacetamide → 3-Amino-4,6-dimethylthieno(2,3-b)pyridine-2-carboxamide

Reaction equation

Br[CH2:2][C:3]([NH2:5])=[O:4].[SH:6][C:7]1[N:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:8]=1[C:9]#[N:10].C[O-].[Na+]>CO>[NH2:10][C:9]1[C:8]2[C:7](=[N:14][C:13]([CH3:15])=[CH:12][C:11]=2[CH3:16])[S:6][C:2]=1[C:3]([NH2:5])=[O:4]

Participants

Procedure

α-Bromoacetamide (388 mg, 2.81 mmol) was added to a solution of 2-mercapto-4,6-dimethyl-nicotinonitrile (420 mg, 2.56 mmol) in MeOH (25 mL) at room temperature. This was followed by addition of sodium methoxide (1.76 mL, 25% NaOMe in MeOH, 7.7 mmol). The reaction mixture was heated to reflux. Heating at reflux was continued overnight, after which time the reaction mixture was cooled and filtered. The product was dried overnight providing 450 mg (80%) of the title compound, m.p. 238-40° C.