Sodium Iodide → 3-ethyl-6-methyl-5-(1,3,4-oxadiazol-2-yl)-1H-pyridin-2-one
Reaction equation
[CH2:1]([C:3]1[C:4]([O:15]C)=[N:5][C:6]([CH3:14])=[C:7]([C:9]2[O:10][CH:11]=[N:12][N:13]=2)[CH:8]=1)[CH3:2].[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[CH2:1]([C:3]1[C:4](=[O:15])[NH:5][C:6]([CH3:14])=[C:7]([C:9]2[O:10][CH:11]=[N:12][N:13]=2)[CH:8]=1)[CH3:2]Participants
Conditions
- Temperature
- 50 °C
Procedure
To a mixture of 3-ethyl-2-methoxy-6-methyl-5-[1,3,4]oxadiazol-2-yl-pyridine (10 mg, 0.0457 mmol) and sodium iodide (19 mg, 0.127 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (2 mL) followed by chlorotrimethylsilane (16.4 μL, 0.131 mmol). The reaction mixture is stirred at 50° C. under nitrogen for 2.5 hr. The reaction mixture is allowed to cool and then quenched with water (0.1 mL). After stirring for 30 min, the mixture is evaporated. The crude residue is purified by flash chromatography on a 2-gram silica gel cartridge by elution with dichloromethane:methanol (49:1). The fraction containing the product is evaporated to give 3-ethyl-6-methyl-5-(1,3,4-oxadiazol-2-yl)-1H-pyridin-2-one (2 mg, 21% yield) as a white solid. LC/MS: RT: 1.98 min, MS: m/e=206 (M+H).
Workup
- temperatureto cool
- customquenched with water (0.1 mL)
- stirringAfter stirring for 30 min
- customthe mixture is evaporated
- customThe crude residue is purified by flash chromatography on a 2-gram silica gel cartridge by elution with dichloromethane:methanol (49:1)
- additionThe fraction containing the product
- customis evaporated
Sources & evidence
- ORD record
- ord-dd270799250b46bea2ae30fedaa4bb1e
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173682B2
Reaction notes
Loading…