Methyl iodide → 6-Amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrile

HRID 1356048Notes

Reaction equation

HRID 1356048 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[S:8])[C:5]([C:9]#[N:10])=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1.[CH3:16][O-].[Na+].CI>CO>[NH2:1][C:2]1[CH:3]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[C:5]([C:9]#[N:10])=[C:6]([S:8][CH3:16])[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 185073536-Amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile

Product 1

HCID 185075176-Amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 150 mg (0.69 mmol) 6-amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile in 3 ml methanol were added 0.13 ml (0.69 mmol) sodium methylate solution (5.4M in ethanol) and 0.04 ml (0.69 mmol) methyl iodide and the reaction mixture stirred at room temperature for 30 minutes. The reaction mixture was then concentrated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether to afford 113 mg (71%) 6-amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrile as a brown crystalline solid. ES-MS m/e (%): 232 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in ether

Sources & evidence

ORD record
ord-1b3792b8994d4589aad7a26e533721d2
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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