Triethylamine → HCID 9921183, compound

HRID 1835821Notes

Reaction equation

HRID 1835821 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH3:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[C:17]1([C:23]#[CH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C)C=O.C(OCC)(=O)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>[CH2:8]([C:5]1[CH:4]=[N:3][C:2]([C:24]#[C:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:7][CH:6]=1)[CH3:9]

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 10821Phenylacetylene2×HCID 35727632-Chloro-5-ethylpyrimidine

Product 1

HCID 9921183HCID 9921183, compoundYield 105.6%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 67553Tetrabutylammonium IodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
47.5 °C

Procedure

2-Chloro-5-ethylpyrimidine (500 mg, 3.5 mmol), PdCl2(PPh3)2 (250 mg, 0.35 mmol), CuI (203 mg, 1.06 mmol), triethylamine (6.0 mL, 43 mmol), and n-Bu4NI (3.85 g, 10.4 mmol) were combined in dimethylformamide (DMF) (30 mL). The mixture was cooled in an ice bath and then phenylacetylene (1.5 mL, 14 mmol) was added. The reaction mixture was then heated to 45-50° C. and after 1.5 h, additional phenylacetylene (1.5 mL, 14 mmol) was added. After an additional 17 h the reaction was diluted with ethyl acetate, washed with brine (4×15 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The resulting black oil was purified by column chromatography eluting with hexane then 90:10 hexane:ethyl acetate to afford 5-ethyl-2-(phenylethynyl)pyrimidine (770 mg, >100%) as a black oil. MS (EI ionization) 208 (M+). This material was carried on to the salt formation without further purification

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. washwashed with brine (4×15 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting black oil was purified by column chromatography
  7. washeluting with hexane

Sources & evidence

ORD record
ord-bbb391fc860b4feeb2c49527d5cfeea2
Source dataset
uspto-grants-2004_08
Patent number
US06774138B2

Reaction notes

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