Dimethylformamide → N'-(5-fluoro-2-methylsulfanylpyrimidin-4-yl)-N,N-dimethylformamidine
Reaction equation
[F:1][C:2]1[C:3]([NH2:10])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[CH3:11][N:12]([CH3:15])[CH:13]=O>C(OCC)C>[F:1][C:2]1[C:3]([N:10]=[CH:11][N:12]([CH3:15])[CH3:13])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-fluoro-2-methylsulfanylpyrimidin-4-ylamine (7.5 g, 47.1 mmol) in N,N-dimethylformamide (DMF; 18 mL) was added DMF-dimethylacetal (DMF-DMA; 8.42 g, 70.7 mmol), and the resulting solution was stirred under nitrogen (N2) for 4 h. The homogeneous solution was diluted with diethyl ether (Et2O; 500 mL), washed with H2O (5×100 mL), and the organic phase was dried over Na2SO4, filtered, and concentrated to a white solid. Recrystallization from hexane afforded N′-(5-fluoro-2-methylsulfanylpyrimidin-4-yl)-N,N-dimethylformamidine (8.47 g, 84%) as white needles: mp 75-77° C.; 1H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 8.12 (d, J=3.1 Hz, 1H), 3.19 (s, 3H), 3.18 (s, 3H), 2.53 (s, 3H); CIMS m/z 214 ([M]+).