Methyl iodide → HCID 86716192, compound

HRID 512166Notes

Reaction equation

HRID 512166 reaction equation
[CH:1]1([CH2:4][CH:5]([C:8]2[CH:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[N:12][CH:13]=2)[C:6]#[N:7])[CH2:3][CH2:2]1.CI.[CH3:20]C([O-])(C)C.[K+]>O1CCOCC1>[CH:1]1([CH2:4][C:5]([CH3:20])([C:8]2[CH:9]=[N:10][C:11]([C:14]([F:16])([F:17])[F:15])=[N:12][CH:13]=2)[C:6]#[N:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 86716193HCID 86716193, compound

Product 1

HCID 86716192HCID 86716192, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-cyclopropyl-2-(2-(trifluoromethyl)pyrimidin-5-yl)propanenitrile (310 mg, 1.29 mmol) and MeI (0.27 g, 1.9 mmol) in dioxane (10 ml) was added t-BuOK (1.39 mL, 1.39 mmol, 1M in THF) dropwise at room temperature under N2. The mixture was stirred for 1 h, then quenched by sat.aq. NH4Cl (10 mL), and extracted with EtOAc(3×10 ml). The organic layer was concentrated under reduced pressure to give crude product, which was purified by column chromatography on silica gel (EtOAc/Petroleum ether=1:4) to give compound the title compound (120 mg, yield: 36%). 1H NMR(CDCl3 varian 400): δ9.02 (s, 2H), 1.92 (d, J=6.8 Hz, 2H), 1.87 (s, 3H), 0.80-0.67 (m, 1H), 0.65-0.56 (m, 1H), 0.55-0.45 (m, 1H), 0.30-0.20 (m, 1H), 0.05-0.04 (m, 1H).

Workup

  1. customquenched by sat.aq
  2. extractionNH4Cl (10 mL), and extracted with EtOAc(3×10 ml)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customto give crude product, which
  5. customwas purified by column chromatography on silica gel (EtOAc/Petroleum ether=1:4)

Sources & evidence

ORD record
ord-8546b5f879b44ad59316374c6d45f479
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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