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2-Bromopyrimidine → 4-Pyrimidin-2-ylethynyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 1038043
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1038043
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]#[CH:22])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>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]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]#[C:22][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]
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Komponenten

5

Edukt 2

HCID 783452-Bromopyrimidine2×HCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylate

Produkt 1

HCID 669398774-Pyrimidin-2-ylethynyl-piperidine-1-carboxylic acid tert-butyl esterAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 178418476
HCID 178418476, Verbindung
Katalysator

Versuchsvorschrift

To a suspension of 2-bromopyrimidine (175 mg, 1.1 mmols), dichlorobis(triphenylphosphine)palladium(II) (35 mg, 0.05 mmols) and CuI (10 mg, 0.05 mmols) was added a solution of 4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester (209 mg, 1 mmol). The mixture was stirred overnight, filtered through Celite, concentrated. The residue was partitioned between ethyl acetate and water, organic layer was isolated, dried (MgSO4), and concentrated. The residue was chromatographed on silica gel eluting with ethyl acetate in hexanes (1:1) to give un-reacted 2-bromopyrimidine (130 mg), then the title compound (23 mg). LCMS m/e (288, M+H).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customorganic layer was isolated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with ethyl acetate in hexanes (1:1)
  8. customto give

Quellen und Nachweise

ORD-Eintrag
ord-e45d7b86119f4a91afdadc37a01a965d
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546404B2

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