Nitronium tetrafluoroborate → 3-Methyl-2-methylsulfanyl-5-nitro-6-pyridin-4-yl-3H-pyrimidin-4-one

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Reaction Steps

3-Methyl-2-methylsulfanyl-6-pyridin-4-yl-3H-pyrimidin-4-one (1.0 g, 4.3 mmol) in 10 mL dry acetonitrile at 0° C. under nitrogen was added nitronium tetrafluoroborate (0.5 M in sulfolane, Aldrich Chemical, 17.2 mL, 8.6 mmol) at such a rate as to not let the internal temperature rise above 5° C. The suspension slowly became a homogeneous solution. The reaction was monitored by mass spec and after 2 h, no remaining starting material was observed. The acetonitrile was removed under reduced pressure and the resulting solution was loaded directly onto 90 g of silica. The product was eluted with 0% to 5% methanol/dichloromethane. M+1=279; NMR (CDCl3) s (3H; 2.7 ppm), s (3H; 3.6 ppm), d (2H; 7.5 ppm), d (2H; 8.7 ppm).

Provenance & Evidence