Tetrahydrofuran → 2-(Dipropylamino)-6-methylpyrimidine-4-carboxylic acid

HRID 349024

Reaktionsgleichung

Reaktionsgleichung von HRID 349024
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[C:5]1[N:10]=[C:9]([C:11]([O:13]C)=[O:12])[CH:8]=[C:7]([CH3:15])[N:6]=1)[CH2:2][CH3:3].C1COCC1.O.[OH-].[Li+]>CO.O>[CH2:16]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]1[N:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[C:7]([CH3:15])[N:6]=1)[CH2:17][CH3:18]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 21086142Methyl 2-(dipropylamino)-6-methylpyrimidine-4-carboxylate

Produkt 1

HCID 210854602-(Dipropylamino)-6-methylpyrimidine-4-carboxylic acidAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To methyl 2-(dipropylamino)-6-methylpyrimidine-4-carboxylate (0.450 g, 1.79 mmol) in MeOH (2 mL), water (1 mL), and THF (1 mL) was added lithium hydroxide monohydrate (0.113 g, 2.68 mmol). The mixture was stirred at room temperature for 1 h and then MeOH and THF were removed under reduced pressure. The pH of the residue was adjusted to approximately 5 and the resulting mixture was extracted with dichloromethane, dried over sodium sulfate, and concentrated to give 2-(dipropylamino)-6-methylpyrimidine-4-carboxylic acid (0.351 g) as a yellow solid.

Aufarbeitung

  1. customMeOH and THF were removed under reduced pressure
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ac4350e5e14e4f219cbf7833fe485c41
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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