Methyl iodide → HCID 55299728, compound

HRID 502415Notes

Reaction equation

HRID 502415 reaction equation
[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[CH3:11][Si](C)(C)[N-][Si](C)(C)C.[Na+].CI>C1COCC1>[CH3:10][C:9]1[C:2]([NH:1][CH3:11])=[N:3][CH:4]=[C:5]([CH:8]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 224828436-Amino-5-methylpyridine-3-carbonitrile

Product 1

HCID 55299728HCID 55299728, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Amino-5-methyl-nicotinonitrile (0.250 g, 1.88 mmol) was dissolved in 2.5 ml of abs. THF and treated at 0° C. with sodium hexamethyldisilazide-solution (1M in THF, 2.07 ml, 1.1 eq.) and, after 5 Min., 3 eq. of methyl iodide (0.35 ml). The mixture was allowed to react for 3 h at ambient temperature. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=6/4) produced 0.225 g of the title compound as off-white solid.

Workup

  1. customto react for 3 h at ambient temperature
  2. additionPouring
  3. extractionice/NH4Cl, twofold extraction with AcOEt
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-339585f7f2f04f8a8cc17efad5200a26
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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