Hydrochloric Acid → HCID 178457455, Verbindung

HRID 2169199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169199
[CH2:1]([O:8][C:9]1[C:10]([C:26]([N:28]([CH2:32][CH2:33][O:34][Si](C(C)(C)C)(C)C)[CH:29]([CH3:31])[CH3:30])=[O:27])=[N:11][C:12]([CH2:16][C:17]([CH3:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>O1CCCC1.O>[CH2:1]([O:8][C:9]1[C:10]([C:26]([N:28]([CH2:32][CH2:33][OH:34])[CH:29]([CH3:31])[CH3:30])=[O:27])=[N:11][C:12]([CH2:16][C:17]([CH3:18])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:25])=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178457489HCID 178457489, Verbindung

Produkt 1

HCID 178457455HCID 178457455, VerbindungAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-(Benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-6-hydroxy-N-isopropyl-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxamide (57) (62 mg, 107 μmol, Eq: 1.00) was stirred in tetrahydrofuran (2 ml), HCl (aqueous) (161 μl, 161 μmol, Eq: 1.5) was added. The reaction mixture was stirred at room temperature for 3.0 hours, 160 μl 1N NaOH was added and the reaction mixture was diluted with water, extracted twice with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Trituration in hexanes/ether was conducted to give 5-(benzyloxy)-6-hydroxy-N-(2-hydroxyethyl)-N-isopropyl-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxamide (58) (32 mg, 64%).

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-1acdde4cdf224d408d757e04a98a4f96
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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