2,4-Dichloropyrimidine → HCID 86687910, compound

HRID 1400063Notes

Reaction equation

HRID 1400063 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[CH2:18][C:19]#[N:20])#[CH:10]>C(#N)C.C(N(CC)CC)C.[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>[Cl:1][C:2]1[N:7]=[C:6]([C:10]#[C:9][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[CH2:18][C:19]#[N:20])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 86687909HCID 86687909, compound

Product 1

HCID 86687910HCID 86687910, compoundYield 65.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

2,4-Dichloropyrimidine (764 mg, 5.13 mmol) is dissolved in degassed acetonitrile (19.700 ml) and triethylamine (19.70 ml). Copper(I) iodide (75 mg, 0.395 mmol) is added, the mixture is degassed again for 10 min., and 2-(2-ethynyl-5-fluorophenyl)acetonitrile (628 mg, 3.95 mmol) and bis(triphenylphosphine)palladium(II) chloride (138 mg, 0.197 mmol) are then added successively to the greenish solution. The reaction phase is warmed at 80° C. for 30 min. The mixture is subsequently worked up, as described above, and the crude mass obtained is purified by chromatography on silica gel (petroleum ether/ethyl acetate=80/20 to 75/25), giving 700 mg of 2-(2-((2-chloropyrimidin-4-yl)ethynyl)-5-fluorophenyl)acetonitrile (2.58 mmol, 65.3% yield) as orange solid;

Workup

  1. customthe mixture is degassed again for 10 min.
  2. customobtained
  3. customis purified by chromatography on silica gel (petroleum ether/ethyl acetate=80/20 to 75/25)

Sources & evidence

ORD record
ord-623d686f80e74068b246c0b669ca5c57
Source dataset
uspto-grants-2014_12
Patent number
US08906916B2

Reaction notes

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