2-(4-Pentynyloxy)tetrahydro-2H-pyran → 5,6-Diphenyl-2-[5-(2-tetrahydropyranyloxy)-1-pentyn-1-yl]pyrazine

HRID 1271301Notes

Reaction equation

HRID 1271301 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:26][CH2:27][CH2:28][CH2:29][C:30]#[CH:31]>C(N(CC)CC)C.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.[Cu]I>[C:8]1([C:5]2[N:6]=[CH:7][C:2]([C:31]#[C:30][CH2:29][CH2:28][CH2:27][O:26][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][O:20]3)=[N:3][C:4]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 3578162-(4-Pentynyloxy)tetrahydro-2H-pyranHCID 36544935-Chloro-2,3-Diphenylpyrazine

Product 1

HCID 229319555,6-Diphenyl-2-[5-(2-tetrahydropyranyloxy)-1-pentyn-1-yl]pyrazineYield 75.8%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

To a solution of 1.58 g of 2-chloro-5,6-diphenylpyrazine in 10 ml of triethylamine, 1.20 g of 5-(2-tetrahydropyranyloxy)-1-pentyne, 208 mg of dichlorobis(triphenylphosphine)palladium (II) and 56 mg of copper (I) iodide were added, followed by stirring under an argon atmosphere at 80° C. for 8 hours. The solvent was evaporated under reduced pressure and the residue was dissolved in diethyl ether, and then the insoluble matter was removed by filtration through celite. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography to obtain 1.79 g of the desired compound as a brown oily substance.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in diethyl ether
  3. customthe insoluble matter was removed by filtration through celite
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-30c9cb5a484e4641a505c92c2d64f0e7
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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