Ethyl Acetate → HCID 178524880, Verbindung

HRID 2169409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169409
C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Br:31])[N:9]=1)=[O:7])(C)(C)C.O[Li].O.C(OCC)(=O)C>O1CCCC1.O.CCCCCC>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Br:31])=[N:11][C:12]=1[OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 178450820HCID 178450820, Verbindung

Produkt 1

HCID 178524880HCID 178524880, VerbindungAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058HexaneLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a stirred solution of 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (376) (14 g, 27.723 mmol) in tetrahydrofuran-water (15:7, 220 mL) was added LiOH.H2O (11.644 g, 277.228 mmol). The reaction mixture was refluxed for 16 h while silica thin layer chromatography was performed (50% ethyl acetate in hexane; Rf=0.1). After completion of the reaction, all volatiles were removed and the residue was diluted with water (50 mL) and neutralized to pH 7 with 1N HCl. The mixture was filtered and the resulting solid was dried to get 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid (377) (11.8 g, 94.65%) as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 16 h while silica thin layer chromatography
  2. customAfter completion of the reaction
  3. customall volatiles were removed
  4. additionthe residue was diluted with water (50 mL)
  5. filtrationThe mixture was filtered
  6. customthe resulting solid was dried

Quellen und Nachweise

ORD-Eintrag
ord-56e78e9572824edbace6c0818f3c002e
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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