Water → Methyl 2-phenylpyrimidine-5-carboxylate

HRID 219635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219635
O.Cl.[C:3]([NH2:11])(=[NH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Na].[CH3:13][O:14][C:15](=[O:24])[C:16]([CH:19](OC)OC)=[CH:17]O.O>CN(C=O)C>[CH3:13][O:14][C:15]([C:16]1[CH:17]=[N:10][C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:11][CH:19]=1)=[O:24]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 5360545SodiumHCID 16219042Benzamidine HCl hydrateHCID 591179393,3-Dimethoxy-2-methoxycarbonylpropen-1-ol

Produkt 1

HCID 11206661Methyl 2-phenylpyrimidine-5-carboxylateAusbeute 74,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of benzamidine hydrochloride hydrate (2 mmol) in anhydrous DMF (4 mL) is added sodium salt of 2-dimethoxymethyl-3-hydroxy-acrylic acid methyl ester (0.46 g, 2.32 mmol) and the reaction mixture heated at 100° C. under N2 for 1 hour. The reaction is cooled to room temperature and water (15 mL) is added. After addition of water, immediate precipitation of the product is observed. The solids are collected by filtration, washed with water (2.5 mL) and vacuum dried to yield 2-phenyl-pyrimidine-5-carboxylic acid methyl ester (0.32 g, 74%). (see: P. Zhichkin, D. J. Fairfax, S. A. Eisenbeis, Synthesis, 2002, 720-722.)

Aufarbeitung

  1. temperatureThe reaction is cooled to room temperature
  2. filtrationThe solids are collected by filtration
  3. washwashed with water (2.5 mL) and vacuum
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2ce903fd898140d1b937271641a88f62
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202863B2

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