Methyl iodide → HCID 755007, compound

HRID 1355705Notes

Reaction equation

HRID 1355705 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[S:8])[C:5]([C:9]#[N:10])=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[C:17]#[N:18].[CH3:19][O-].[Na+].CI>CO>[NH2:1][C:2]1[C:3]([C:17]#[N:18])=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([C:9]#[N:10])=[C:6]([S:8][CH3:19])[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 780902NSC678060HCID 10942334Sodium Methoxide

Product 1

HCID 755007HCID 755007, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 0.19 g (0.75 mmol) 6-amino-4-phenyl-2-thioxo-1,2-dihydro-pyridine-3,5-dicarbonitrile in 25 ml methanol were added 0.14 ml (0.76 mmol) sodium methylate solutiuon (5.4M in methanol) and 0.09 ml (1.5 mmol) methyl iodide and stirring continued for 16 hours at room temperature. The reaction mixture was then cooled to 0° C. and the resulting crystals collected by filtration and washed with ether/methanol (3/1) to afford 0.1 g (50%) 2-amino-6-methylsulfanyl-4-phenyl-pyridine-3,5-dicarbonitrile as a white crystalline solid. EI-MS m/e (%): 266 (M+, 40), 265 ([M—H]+, 100).

Workup

  1. filtrationthe resulting crystals collected by filtration
  2. washwashed with ether/methanol (3/1)

Sources & evidence

ORD record
ord-4f6d767892904fa488ba619c3fb94d82
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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