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2-Chloro-4,6-dimethoxy-5-nitropyrimidine → 2-(4-Fluoro-benzyl)-4,6-dimethoxy-5-nitro-pyrimidine

HRID 334998
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 334998
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([O:13][CH3:14])[N:3]=1.[Cl-].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][Zn+])=[CH:19][CH:18]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][C:2]2[N:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([O:13][CH3:14])[N:3]=2)=[CH:19][CH:18]=1
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Komponenten

5

Edukt 2

HCID 109985372-Chloro-4,6-dimethoxy-5-nitropyrimidineHCID 178505764HCID 178505764, Verbindung

Produkt 1

HCID 576951302-(4-Fluoro-benzyl)-4,6-dimethoxy-5-nitro-pyrimidineAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

(26) A solution of compound (25) (1.2 g, 5.5 mmol), 4-fluorobenzylzinc chloride (13.1 mL, 0.5 M in THF, 6.6 mmol), tetrakis(triphenylphosphine)palladium (0.13 g, 0.1 mmol) in THF (50 mL) was heated to refluxed for 3 hours under nitrogen. After it cooled to room temperature, the THF was removed in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4. After concentrated, the residue was purified by a column chromatography on silica gel eluting with 5% ethyl acetate in hexane to yield 2-(4-fluoro-benzyl)-4,6-dimethoxy-5-nitro-pyrimidine (26) (1.1 g, 63%). 1H NMR (CDCl3)

Aufarbeitung

  1. temperatureto refluxed for 3 hours under nitrogen
  2. customthe THF was removed in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrated
  7. customthe residue was purified by a column chromatography on silica gel eluting with 5% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-992b50dee6734a169c3ec7f10fa27b8c
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883833B2

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