Ethyl Acetate → tert-butyl ((1S,3R)-3-((2-chloro-4-methoxypyrimidin-5-yl)ethynyl)cyclohexyl)carbamate

HRID 2284787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2284787
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5](I)=[CH:4][N:3]=1.[C:11]([C@@H:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:14]1)#[CH:12].C(OCC)(=O)C.[Cl-].[NH4+]>CN(C)C=O.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>[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:12]#[C:11][C@@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:14]2)=[CH:4][N:3]=1

Komponenten

9

Edukt 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 151888882-Chloro-5-iodo-4-methoxypyrimidineHCID 90051794tert-butyl ((1S,3R)-3-ethynylcyclohexyl)carbamate

Produkt 1

HCID 117861333tert-butyl ((1S,3R)-3-((2-chloro-4-methoxypyrimidin-5-yl)ethynyl)cyclohexyl)carbamateAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-5-iodo-4-methoxypyrimidine (Q1, 101 mg), tert-butyl ((1S,3R)-3-ethynylcyclohexyl)carbamate (P0, 100 mg), bis(triphenylphosphine)palladium(II) dichloride (26 mg) and copper(I) iodide (14 mg) in N,N-dimethylformamide (3 mL), triethylamine (258 μL) was added at room temperature, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture, ethyl acetate and saturated aqueous ammonium chloride were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 88 to 50% hexane in ethyl acetate) to obtain tert-butyl ((1S,3R)-3-((2-chloro-4-methoxypyrimidin-5-yl)ethynyl)cyclohexyl)carbamate (Q2, 118 mg).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 88 to 50% hexane in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2969d906fae1443cbb5b8aeee917db53
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145415B2

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