5-Bromo-2-(3,3-dimethylbut-1-yn-1-yl)pyrimidine → HCID 57804136, compound

HRID 2102904Notes

Reaction equation

HRID 2102904 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]#[C:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.[Cu](C#N)[C:15]#[N:16]>CN1CCCC1>[CH3:11][C:10]([CH3:13])([CH3:12])[C:9]#[C:8][C:5]1[N:4]=[CH:3][C:2]([C:15]#[N:16])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 578042095-Bromo-2-(3,3-dimethylbut-1-yn-1-yl)pyrimidineHCID 178418260HCID 178418260, compound

Product 1

HCID 57804136HCID 57804136, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 5-bromo-2-(3,3-dimethylbut-1-ynyl)pyrimidine (2.5 g, 0.010 mol) and copper cyanide (1.4 g, 0.016 mol) in N-methyl pyrrolidine was heated in a sealed tube at 200° C. for 24 hours. The mixture was allowed to cool to room temperature and filtered through Celite® and the filtrate was concentrated under vaccum. The residue was purified by column chromatography on silica gel with an ethyl acetate: hexane (0-50% gradient) to give the product (1.25 g).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through Celite®
  3. concentrationthe filtrate was concentrated under vaccum
  4. customThe residue was purified by column chromatography on silica gel with an ethyl acetate

Sources & evidence

ORD record
ord-7f727b782e1643579291df3acda1962d
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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