Propyne → HCID 22027559, compound

HRID 1474034Notes

Reaction equation

HRID 1474034 reaction equation
[CH:1]#[C:2][CH3:3].Cl[C:5]1[N:10]=[C:9](Cl)[CH:8]=[CH:7][N:6]=1>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCN(CC)CC>[C:1]([C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1)#[C:2][CH3:3]

Participants

6

Reactant 2

HCID 6335PropyneHCID 775312,4-Dichloropyrimidine

Product 1

HCID 22027559HCID 22027559, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Using a high pressure tube, propyne (5 mL) was condensed in a mixture of 2,4-dichloro-pyrimidine (1.71 g, 11.47 mmol), CuI (228 mg, 1.20 mmol), Pd(PPh3)2Cl2 (0.57 mmol), and Et3N (50 mL) at −78° C. The mixture was slowly warmed up and stirred at room temperature for 12 h. After this period, the mixture was quenched with aqueous NH4Cl. The aqueous phase was thoroughly extracted with hexanes. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4; and concentrated under reduced pressure. The residue was purified by silica gel chromatography with 5%-15% EtOAc/hexanes to give 19 (1.64 g, 94%).

Workup

  1. customcondensed
  2. temperatureThe mixture was slowly warmed up and
  3. waitAfter this period
  4. customthe mixture was quenched with aqueous NH4Cl
  5. extractionThe aqueous phase was thoroughly extracted with hexanes
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationand concentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography with 5%-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-3e33bb5379804bf5ac32150291a8e22e
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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