Diisopropylethylamine → HCID 86730180, Verbindung

HRID 1850143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850143
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[CH:5]=[CH:4][N:3]=1.Cl.C[NH:19][CH2:20][C:21]#[CH:22].[CH:23](N(C(C)C)CC)(C)C>CS(C)=O.CCOC(C)=O>[CH:13]([C@H:12]1[CH2:11][O:10][C:9](=[O:16])[N:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:19][C@@H:20]([CH3:23])[C:21]#[CH:22])[N:7]=1)([CH3:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 22416630HCID 22416630, VerbindungHCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Produkt 1

HCID 86730180HCID 86730180, VerbindungAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of compound (S)-3-(2-Chloro-pyrimidin-4-yl)-4-isopropyl-oxazolidin-2-one (1.03 g, 4.3 mmol) in DMSO (12 mL) was added methyl-prop-2-ynylamine HCl salt (450 mg, 4.3 mmol) and diisopropylethylamine (2.2 mL, 12.6 mmol). The reaction was heated to 110 C for 18 hours. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (25 mL) and brine (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified on silica gel column chromatography (EtOAc/Heptane 0 to 75%) provided (S)-4-Isopropyl-3-[2-((S)-1-methyl-prop-2-ynylamino)-pyrimidin-4-yl]-oxazolidin-2-one (360 mg) in 31% yield. LC-MS m/z: 275.1 (M−Boc)+; RT.: 1.33 min.

Aufarbeitung

  1. temperatureThe reaction was heated to 110 C for 18 hours
  2. washwashed with water (25 mL) and brine (25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified on silica gel column chromatography (EtOAc/Heptane 0 to 75%)

Quellen und Nachweise

ORD-Eintrag
ord-259f04e011174aee9ae63a5f71dad13e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957068B2

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