Methyl iodide → HCID 2835646, compound

HRID 1355823Notes

Reaction equation

HRID 1355823 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)[C:3]=1[C:16]#[N:17].[CH3:18][O-].[Na+].CI>CO>[NH2:1][C:2]1[C:3]([C:16]#[N:17])=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[C:5]([C:9]#[N:10])=[C:6]([S:8][CH3:18])[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 764895HCID 764895, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 2835646HCID 2835646, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 210 mg (0.87 mmol) 6-amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3,5-dicarbonitrile in 25 ml methanol were added 0.16 ml (0.87 mmol) sodium methylate solutiuon (5.4M in methanol) and 0.11 ml (1.73 mmol) methyl iodide and stirring continued for 90 minutes at room temperature. The reaction mixture was then poured onto 100 ml ice-water and the resulting crystals collected by filtration and dried in vacuo to afford 135 mg (61%) 2-amino-4-furan-2-yl-6-methylsulfanyl-pyridine-3,5-dicarbonitrile as a light brown crystalline solid. EI-MS m/e (%): 256 (M+, 49), 255 ([M—H]+, 100).

Workup

  1. filtrationthe resulting crystals collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-6af9180a59904f689118a4849f3bb8a3
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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