Methyl iodide → HCID 68455945, compound

HRID 502423Notes

Reaction equation

HRID 502423 reaction equation
C(OC1C=C(C=C(OCC)C=1F)CN1CCC([NH:14][C:15](=O)[C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([NH:23][CH3:24])=[N:18][CH:17]=2)CC1)C.[CH3:33][Si](C)(C)[N-][Si](C)(C)C.[Na+].CI>C1COCC1>[CH3:33][N:23]([CH3:24])[C:19]1[C:20]([CH3:22])=[CH:21][C:16]([C:15]#[N:14])=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68456849HCID 68456849, compound

Product 1

HCID 68455945HCID 68455945, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-6-methylamino-nicotinonitrile (example 121, 0.345 g, 2.34 mmol) was dissolved in 3.2 ml of abs. THF and treated at 0° C. with sodium hexamethyldisilazide-solution (1M in THF, 7.03 ml, 3.0 eq.) and, after 5 Min., 4 eq. of methyl iodide (0.58 ml). The mixture was allowed to react for 1 h at room 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=7/3) yielded 0.330 g of the title compound as off-white solid.

Workup

  1. customto react for 1 h at room 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-364f43e48b7f47ca937c321938196f03
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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