Dimethylformamide dimethyl acetal → HCID 67983763, Verbindung

HRID 2359731

Reaktionsgleichung

Reaktionsgleichung von HRID 2359731
[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.[CH3:16][N:17]([CH:19](OC)OC)[CH3:18]>>[CH:1]1([CH2:4][C:5](=[O:15])/[C:6](/[C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=2)=[CH:16]\[N:17]([CH3:19])[CH3:18])[CH2:3][CH2:2]1

Komponenten

3

Edukt 2

HCID 78373Dimethylformamide dimethyl acetalHCID 679835361-Cyclopropyl-3-[2-(methylsulfanyl)pyrimidin-4-yl]propan-2-one

Produkt 1

HCID 67983763HCID 67983763, VerbindungAusbeute 69,2 %

Versuchsvorschrift

A solution of 1-cyclopropyl-3-[2-(methylsulfanyl)pyrimidin-4-yl]propan-2-one (2) (216.3 mg, 0.973 mmol) in DMF-DMA (1303 μl, 9.73 mmol) was stirred at 80° C. for 2 hours. The reaction was partitioned between water and EtOAc. The organic layer was separated, 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 [25 g ISOLUTE column, 100% DCM to 10% MeOH/DCM] to obtain the desired product as a orange-yellow solid (186.8 mg, 69.2% yield). MS (ES+): m/z=278.2/279.2 (100/50) [MH+]. HPLC: tR=0.99 minute over 3 minutes. Purity: 100% [HPLC (LC/MS) at 220 nm].

Aufarbeitung

  1. customThe reaction was partitioned between water and EtOAc
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back-extracted
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by Biotage™ silica gel chromatography [25 g ISOLUTE column, 100% DCM to 10% MeOH/DCM]

Quellen und Nachweise

ORD-Eintrag
ord-67f592935ec74b06a51b22822eb8cf8f
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685993B2

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