Hydrochloric Acid → 6-(Methoxymethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylic acid

HRID 1426316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426316
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].BrC[C:9]1[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]=[C:11]([C:19]([O:21][CH2:22]C)=O)[CH:10]=1.Cl>CO.O>[CH3:22][O:21][CH2:19][C:11]1[N:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[N:14]=[C:9]([C:1]([OH:2])=[O:4])[CH:10]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 58431340Ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate

Produkt 1

HCID 696732866-(Methoxymethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Potassium carbonate (1.2 g, 8.7 mmol) was added to a solution of ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate (0.65 g, 1.2 mmol, prepared in the manner outlined in Example 47, Step A) in methanol (10 mL). After stirring for 2 hours, the reaction was then treated with 1N HCl to achieve pH 4, was diluted with water and extracted with six portions of 10% isopropanol in chloroform. The combined extracts were dried over sodium sulfate and concentrated to afford product as an oil which was used without further purification (0.25 g, 88%). 1H NMR (300 MHz, CDCl3) δ 8.48 (s, 1H), 4.74 (s, 2H), 3.58 (s, 3H); LCMS (M+H)+: 237.1.

Aufarbeitung

  1. customprepared in the manner
  2. extractionextracted with six portions of 10% isopropanol in chloroform
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto afford product as an oil which
  6. customwas used without further purification (0.25 g, 88%)

Quellen und Nachweise

ORD-Eintrag
ord-e082c98a6d074afebb141fe3d2e39f9c
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933085B2

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