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Sodium Hydroxide → 2-(4-Methyl-2-phenyl-6-p-tolylpyrimidin-5-yl)pentanoic acid

HRID 1399585
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1399585
[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11]C)=[O:10])=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[N:5]=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:3]=1.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([OH:11])=[O:10])=[C:6]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[N:5]=[C:4]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 50994994Methyl 2-(4-methyl-2-phenyl-6-p-tolylpyrimidin-5-yl)pentanoate

Produkt 1

HCID 509976972-(4-Methyl-2-phenyl-6-p-tolylpyrimidin-5-yl)pentanoic acidAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of methyl 2-(4-methyl-2-phenyl-6-p-tolylpyrimidin-5-yl)pentanoate (80 mg; 0.214 mmol) in tetrahydrofuran (2.136 mL) was added a 10 N sodium hydroxide solution (214 μL; 2.136 mmol) and the mixture was heated at 100° C. for 18 h. The volatiles were removed under reduced pressure and the mixture was acidified by adding 6N hydrochloric acid. The suspension was extracted twice with ethyl acetate. The combined organic layers were washed with a saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure to give 31 mg (40%) of the title compound as a white solid. ESI/APCI(+): 361 (M+H).

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. additionby adding 6N hydrochloric acid
  3. extractionThe suspension was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-47fc2dc2311c4d218d3079fd49f6078c
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906906B2

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