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

HRID 2284784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2284784
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5](I)=[CH:4][N:3]=1.[C:13]([C@@H:15]1[CH2:20][CH2:19][CH2:18][C@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:16]1)#[CH:14].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]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:14]#[C:13][C@@H:15]2[CH2:20][CH2:19][CH2:18][C@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:16]2)=[CH:4][N:3]=1

Komponenten

9

Edukt 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 900517702-chloro-5-iodo-N-propylpyrimidin-4-amineHCID 90051794HCID 90051794, Verbindung

Produkt 1

HCID 90052871tert-butyl ((1S,3R)-3-((2-chloro-4-(propylamino)pyrimidin-5-yl)ethynyl)cyclohexyl)carbamateAusbeute 80,6 %

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-N-propylpyrimidin-4-amine (F1, 78 mg), bis(triphenylphosphine)palladium(II) dichloride (18 mg) and copper(I) iodide (10 mg) in N,N-dimethylformamide (2 mL), triethylamine (181 μL) and tert-butyl ((1S,3R)-3-ethynylcyclohexyl)carbamate (P0, 70 mg) were added at room temperature, and the mixture was stirred at the same temperature for 8 hours. To the reaction mixture, ethyl acetate and saturated aqueous ammonium chloride were added. The organic layer was separated, washed successively with saturated aqueous ammonium chloride, 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, 94 to 60% hexane in ethyl acetate) to obtain tert-butyl ((1S,3R)-3-((2-chloro-4-(propylamino)pyrimidin-5-yl)ethynyl)cyclohexyl)carbamate (P1, 83 mg).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed successively with saturated aqueous ammonium chloride, 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, 94 to 60% hexane in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-52e30b96c4464866b683402fed5857c2
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145415B2

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