Methyl iodide → 6-Amino-4-methoxy-2-methylnicotinonitrile

Participants

Reaction Steps

To a mixture of sodium 6-amino-3-cyano-2-methylpyridin-4-olate (500 mg, 2.92 mmol, prepared in analogy to WO2001062233A2 and isolated as sodium salt), and K2CO3 (808 mg, 5.84 mmol) in DMF (1 ml) was added MeI (0.200 ml, 3.21 mmol), and the reaction mixture was stirred at it for 9 d. Saturated NaHCO3 (50 ml) was added and the mixture was extracted with EA (4×20 ml). The combined organic extracts were diluted with additional DCM and MeOH until homogeneous, dried over Na2SO4, filtered and concentrated. The crude product was recrystallized from refluxing MeOH-DCM to afford the title compound. 1H-NMR (DMSO-d6, 400 MHz): 2.34 (s, 3H), 3.82 (s, 3H), 5.91 (s, 1H), 6.83 (br, s, 2H); LCMS RtM=1.11 min, [M+H]+=164.2.

Provenance & Evidence