Water → 1-(5-bromomethyl-pyrazin-2-yl)-5-chloro-1H-pyridin-2-one

HRID 1421730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421730
C1C(=O)N([Br:8])C(=O)C1.CSC.[Cl:12][C:13]1[CH:14]=[CH:15][C:16](=[O:27])[N:17]([C:19]2[CH:24]=[N:23][C:22]([CH2:25]O)=[CH:21][N:20]=2)[CH:18]=1.O>C(Cl)Cl>[Br:8][CH2:25][C:22]1[N:23]=[CH:24][C:19]([N:17]2[CH:18]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]2=[O:27])=[N:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 67184N-bromobutanimideHCID 187797445-chloro-1-(5-hydroxymethyl-pyrazin-2-yl)-1H-pyridin-2-one

Produkt 1

HCID 187796991-(5-bromomethyl-pyrazin-2-yl)-5-chloro-1H-pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a slurry of NBS (0.598 g, 3.36 mmol) in CH2Cl2 (10 ml) at 0° C. was added methylsulfide (0.296 ml, 4.035 mmol). The slurry was cooled to -20° C. and the alcohol from step 3 (0.532 g, 2.24 mmol) was added followed by CH2Cl2 (10 ml). The reaction was stirred at 0° C. for 3 hrs and then at room temperature for 24 hrs. The reaction was poured into water and extracted into CH2Cl2 and the combined extracts were dried (MgSO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc: CH2Cl2 30:70) to afford the title compound.

Aufarbeitung

  1. waitat room temperature for 24 hrs
  2. extractionextracted into CH2Cl2
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (silica gel, EtOAc: CH2Cl2 30:70)

Quellen und Nachweise

ORD-Eintrag
ord-d66a57bc78bc4d9d9cb430dd81251735
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06077853

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