4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile → 4-[1,1-Dimethyl-3-(2-pyrimidinyl)-2-propynyloxy]benzonitrile

HRID 1073948Notes

Reaction equation

HRID 1073948 reaction equation
[CH3:1][C:2]([CH3:14])([O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[C:3]#[CH:4].I[C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1>C(N(CC)CC)C.[Pd](Cl)Cl.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]([CH3:14])([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=1)[C:3]#[C:4][C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

7

Reactant 2

HCID 27790724-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrileHCID 113562002-Iodopyrimidine

Product 1

HCID 198955894-[1,1-Dimethyl-3-(2-pyrimidinyl)-2-propynyloxy]benzonitrileYield 64.8%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

0.63 g of 4-(1,1-dimethyl-2-propynyloxy)benzonitrile, 0.75 g of 2-iodopyrimidine, 18 mg of triphenylphosphine, 12 mg of palladium(II) chloride and 3.5 mg of copper(I) iodide were stirred overnight in 20 ml of triethylamine under nitrogen. The mixture was evaporated to dryness and then ethyl acetate and water were added. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:3) and subsequently ethyl acetate/petroleum ether (1:1) for the elution. There were obtained 580 mg of 4-[1,1-dimethyl-3-(2-pyrimidinyl)-2-propynyloxy]benzonitrile as an oil.

Workup

  1. customThe mixture was evaporated to dryness
  2. additionethyl acetate and water were added
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-567be858ccc245f8be7754c356f57004
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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