Triethylamine → HCID 89529909, compound

HRID 715900Notes

Reaction equation

HRID 715900 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[C:9]([O:15][CH3:16])(=[O:14])[CH2:10][CH2:11][C:12]#[CH:13].C(N(CC)CC)C.[Cl-].[NH4+]>CN(C)C=O.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:5]1[N:4]=[CH:3][C:2]([C:13]#[C:12][CH2:11][CH2:10][C:9]([O:15][CH3:16])=[O:14])=[CH:7][N:6]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 543061Methyl 4-pentynoateHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 89529909HCID 89529909, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 500 mg (2.58 mmol) of 5-bromo-2-chloropyrimidine in 10 ml of N,N-dimethylformamide, 397 mg (3.54 mmol) of methyl 4-pentinoate, which was synthesized by the method described in W. D. Wulff et al., Journal of the American Chemical Society, 1988, Vol. 110, pp. 7419-7434, 49 mg (0.26 mmol) of copper iodide, 149 mg (0.129 mmol) of tetrakis(triphenylphosphine)palladium (0) and 5.0 ml of triethylamine were added, and the reaction solution was stirred at 80° C. for 4 hours. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=93/7-75/25 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 347 mg (yield: 60%) of methyl 5-(2-chloropyrimidin-5-yl)-4-pentinoate.

Workup

  1. additionwas added to the reaction solution
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-1f0a329a1ecb4d0f9a23cf6f613515f2
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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