Sodium Iodide → HCID 178435580, compound

HRID 1921369Notes

Reaction equation

HRID 1921369 reaction equation
[CH2:1]([C:3]1[C:4]([O:16]C)=[N:5][C:6]([CH3:15])=[C:7]([C:9]2[N:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[CH:8]=1)[CH3:2].[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[CH2:1]([C:3]1[C:4](=[O:16])[NH:5][C:6]([CH3:15])=[C:7]([C:9]2[NH:10][N:11]=[C:12]([CH3:14])[N:13]=2)[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397Chlorotrimethylsilane2×HCID 674921003-ethyl-2-methoxy-6-methyl-5-(5-methyl-1H-1,2,4-triazol-3-yl)pyridine

Product 1

HCID 178435580HCID 178435580, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(5-methyl-1H-1,2,4-triazol-3-yl)pyridine (90 mg, 0.413 mmol) and sodium iodide (194 mg, 1.29 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (5 mL) followed by drop-wise addition of chlorotrimethylsilane (162 μL, 1.29 mmol). The reaction mixture is stirred at 60° C. under nitrogen for 12 hr. LC/MS shows the reaction is incomplete. Further chlorotrimethylsilane (100 μL) is added and heating continued for 6 hr. The reaction mixture is allowed to cool and then quenched with water (0.7 mL). After stirring for 30 min the reaction mixture is evaporated to dryness. The residue is purified by flash chromatography on a 5-gram silica gel cartridge by elution with 2-propanol. Fractions containing the product are combined, evaporated, triturated with acetonitrile and re-purified by flash chromatography on a 5-gram silica gel cartridge by elution with 2-propanol. Fractions containing the product are combined and the solvent evaporated. The resulting residue is triturated with acetonitrile to give 3-ethyl-6-methyl-5-(5-methyl-2H-1,2,4-triazol-3-yl)-1H-pyridin-2-one (47 mg, 50% yield) as a cream solid. LC/MS: RT: 1.77 min, MS: m/e=219 (M+H); 1H NMR (δ, ppm): 13.99 (1H, s), 11.59 (1, br.s), 7.78 (1H, s), 2.41 (2H, q), 2.37 (3H, s), 1.10 (3H, t).

Workup

  1. temperatureheating
  2. waitcontinued for 6 hr
  3. temperatureto cool
  4. customquenched with water (0.7 mL)
  5. stirringAfter stirring for 30 min the reaction mixture
  6. customis evaporated to dryness
  7. customThe residue is purified by flash chromatography on a 5-gram silica gel cartridge by elution with 2-propanol
  8. additionFractions containing the product
  9. customevaporated
  10. customtriturated with acetonitrile
  11. customre-purified by flash chromatography on a 5-gram silica gel cartridge by elution with 2-propanol
  12. additionFractions containing the product
  13. customthe solvent evaporated
  14. customThe resulting residue is triturated with acetonitrile

Sources & evidence

ORD record
ord-bbfe8af2d1284c7f9ba174ed8b9a4c2b
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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