Lithium hydroxide, monohydrate → 2-methyl-4-(1-methyl-1H-indol-5-yl)pyrimidine-5-carboxylic acid

HRID 1930388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930388
C(O)C.O.O1CCOCC1.[CH3:11][C:12]1[N:17]=[C:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23]([CH3:27])[CH:22]=[CH:21]3)[C:15]([C:28]([O:30]CC)=[O:29])=[CH:14][N:13]=1.O.[OH-].[Li+]>C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:11][C:12]1[N:17]=[C:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23]([CH3:27])[CH:22]=[CH:21]3)[C:15]([C:28]([OH:30])=[O:29])=[CH:14][N:13]=1

Komponenten

6

Edukt 3

HCID 168937Lithium hydroxide, monohydrateHCID 69037048ethyl 2-methyl-4-(1-methyl-1H-indol-5-yl)pyrimidine-5-carboxylateHCID 69104347Dioxane ethanol water

Produkt 1

HCID 690369112-methyl-4-(1-methyl-1H-indol-5-yl)pyrimidine-5-carboxylic acidAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 311Citric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a mix of ethanol:water:dioxane (1:1:1, 9 mL) was placed ethyl 2-methyl-4-(1-methyl-1 H-indol-5-yl)pyrimidine-5-carboxylate (391 mg, 1.324 mmol) and lithium hydroxide hydrate (222 mg, 5.30 mmol). The mix stirred at RT overnight. The mix was diluted with ethyl acetate (25 mL) and 5% citric acid (20 mL). The organic phase was separated, washed with brine (20 mL) and dried over sodium sulfate. The solvent was evaporated at reduced pressure to give 2-methyl-4-(1-methyl-1 H-indol-5-yl)pyrimidine-5-carboxylic acid as a tan solid (132 mg, 37% yield). MS (ESI) m/z: 268.0 (M+H+).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9589b9b47fe84d4991e60260722f9d8e
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188113B2

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