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

HRID 1826514Notes

Reaction equation

HRID 1826514 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:4]=[C:3]1[S:15][CH3:16].F[B-](F)(F)F.[O:22]=[N+:23]=[O:24]>C(#N)C>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N+:23]([O-:24])=[O:22])=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:4]=[C:3]1[S:15][CH3:16]

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 155215183-methyl-2-methylsulfanyl-6-pyridin-4-yl-3H-pyrimidin-4-one

Product 1

HCID 221396093-Methyl-2-methylsulfanyl-5-nitro-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  1. customrise above 5° C
  2. customThe acetonitrile was removed under reduced pressure
  3. washThe product was eluted with 0% to 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-d232b068478d4c459e3ed4ce064757e4
Source dataset
uspto-grants-2006_05
Patent number
US07049318B2

Reaction notes

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