Br[C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cu][C:11]#[N:12]>CN(C=O)C.CCOC(C)=O.O>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:11]#[N:12])=[C:3]([CH3:9])[CH:4]=1A mixture of 5-bromo-4-methyl-2-pyridinamine (0.50 g, 2.7 mmol) and copper (I) cyanide (0.263 g, 2.9 mmol) in DMF (12 mL) was heated at 200° C. for a total of 1.75 h in a microwave reactor. The reaction mixture was diluted with EtOAc and water. The resulting thick dark precipitate was filtered off. The filtrate was extracted with EtOAc (×3) and the combined extracts were dried and concentrated to give a dark yellow solid (0.115 g). The filter cake was and washed with 1:1 DCM/MeOH (1 L) which was concentrated to give a second batch of dark yellow solid (0.047 g). The filter cake was washed with 2M NH3 in MeOH (200 mL) which was concentrated to give a dark green solid (0.533 g). These 3 batches of solids were purified by column chromatography using 0-100% EtOAc/hexane as the eluent to give the title compound as a white solid (total yield: 0.213 g). δH (CDCl3, 400 MHz) 8.28 (1H, s), 6.36 (1H, s), 4.87 (2H, br.s), 2.40 (3H, s). MS (ES): MH+ 134.1.
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