Cesium carbonate → 2-Methylthio-4-chloro-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine

HRID 1290661

Reaktionsgleichung

Reaktionsgleichung von HRID 1290661
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:24]#[N:25]>C(#N)C>[CH3:13][S:12][C:4]1[N:5]=[C:6]([Cl:11])[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([O:20][C:21]2[CH:22]=[C:23]([C:24]#[N:25])[CH:26]=[CH:27][C:28]=2[O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 113454584,6-Dichloro-2-(methylthio)-5-nitropyrimidineHCID 154534514-(Benzyloxy)-3-hydroxybenzonitrile

Produkt 1

HCID 221029862-Methylthio-4-chloro-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidineAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 4,6-dichloro-5-nitro-2-methylthiopyrimidine (5.0 g, 20.8 mmol) in 200 mL acetonitrile at 0° C. was added cesium carbonate (8.82 g, 27.1 mmol) followed by the addition of 3-hydroxy-4-benzyloxybenzonitrile (4.69 g, 20.8 mmol), and the resulting reaction mixture was stirred for 16 hours. The volatiles were evaporated and the residue chromatographed on silica gel (hexane/ethyl acetate, 2:1) to afford 5.0 g of 2-methylthio-4-chloro-5-nitro-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine, a compound of formula (C).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated
  3. customthe residue chromatographed on silica gel (hexane/ethyl acetate, 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-0b7ff376d41f4e619d1270c59be0e6ba
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753635

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