Methyl iodide → HCID 86729993, compound

HRID 2199771Notes

Reaction equation

HRID 2199771 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[N:13]([CH3:14])[N:12]=[N:11][N:10]=2)=[N:6][CH:7]=1.[CH3:15]C([O-])(C)C.[K+].IC>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH3:15])[C:9]2[N:13]([CH3:14])[N:12]=[N:11][N:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 86729994HCID 86729994, compound

Product 1

HCID 86729993HCID 86729993, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

5-bromo-N-(1-methyl-1H-tetrazol-5-yl)pyridine-2-amine (1 g, 3.9 mmol) was dissolved in 50 mL THF, potassium tert-butylate (0.88 g, 7.8 mmol) and iodomethane (1.1 g, 7.8 mmol) were added slowly. The reaction was heated to 70° C. and reacted for 12 h. After filtration and concentration, 330 mg of product was obtained by separation on a silica gel column (dichloromethane:methanol=100:1), at a yield of 31%.

Workup

  1. customreacted for 12 h
  2. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-45248626c7ad48e8898e669b364b6589
Source dataset
uspto-grants-2016_06
Patent number
US09359344B2

Reaction notes

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