Methyl iodide → HCID 86716195, compound

HRID 512168Notes

Reaction equation

HRID 512168 reaction equation
[CH:1]1([CH2:4][CH:5]([C:8]2[CH:9]=[N:10][CH:11]=[N:12][CH:13]=2)[C:6]#[N:7])[CH2:3][CH2:2]1.CI.[CH3:16]C([O-])(C)C.[K+]>O1CCOCC1>[CH:1]1([CH2:4][C:5]([CH3:16])([C:8]2[CH:9]=[N:10][CH:11]=[N:12][CH:13]=2)[C:6]#[N:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 86716194HCID 86716194, compound

Product 1

HCID 86716195HCID 86716195, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-cyclopropyl-2-(pyrimidin-5-yl)propanenitrile (1.5 g, 8.67 mmol) and MeI (1.45 g, 13.0 mmol) in 1,4-dioxane (20 ml) was added t-BuOK (9.57 ml, 9.57 mmol) dropwise at room temperature under N2. The mixture was stirred for 1 h at room temperature then quenched by sat.aq NH4Cl (20 ml) and extracted with EtOAc (3×30 ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give 3-cyclopropyl-2-methyl-2-(pyrimidin-5-yl)propanenitrile (1.5 g), which was used directly for next step.

Workup

  1. customthen quenched by sat.aq NH4Cl (20 ml)
  2. extractionextracted with EtOAc (3×30 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9fd6ea0bee9444989e0cf7811310f22
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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