m-Chloroperbenzoic acid → HCID 67983470, Verbindung

HRID 1397150

Reaktionsgleichung

Reaktionsgleichung von HRID 1397150
[CH:1]1([CH2:4][C:5](=[O:15])[CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C(Cl)Cl>[CH:1]1([CH2:4][C:5](=[O:15])[CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13]([CH3:14])=[O:24])[N:8]=2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 679835361-Cyclopropyl-3-[2-(methylsulfanyl)pyrimidin-4-yl]propan-2-one

Produkt 1

HCID 67983470HCID 67983470, VerbindungAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-cyclopropyl-3-[2-(methylsulfanyl)pyrimidin-4-yl]propan-2-one (2) (3.00 g, 13.49 mmol) in DCM (54.0 mL) at rt, mCPBA (3.99 g, 16.19 mmol) was added in portions. The reaction mixture was stirred at rt for 1 hour. The reaction was partitioned between saturated sodium carbonate solution and DCM and the aqueous layer was back-extracted. The organic extracts were combined, washed with brine, dried over sodium sulfate, then concentrated in vacuo. The crude product was purified by Biotage™ silica gel chromatography [100% DCM to 5% MeOH/DCM] to afford the desired product as a viscous yellow oil (1.88 g, 58.5% yield), which was still contaminated with residual m-chlorobenzoic acid and carried on to the next step. MS (ES+): m/z=239.2 (100) [MH+2]. HPLC: tR=0.73 minute over 3 minutes. Purity: 67.7% [HPLC (LC/MS) at 220 nm].

Aufarbeitung

  1. customThe reaction was partitioned between saturated sodium carbonate solution and DCM
  2. extractionthe aqueous layer was back-extracted
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by Biotage™ silica gel chromatography [100% DCM to 5% MeOH/DCM]

Quellen und Nachweise

ORD-Eintrag
ord-cfbaadf6ef494bf1a91d5e9fa5ca9932
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901147B2

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