Isobutylamine → 7-amino-2,2-dimethyl-8-(2-methylpropyl)-6-nitroso-3H-imidazo[1,2-a]pyrimidin-5-one

HRID 236023

Reaktionsgleichung

Reaktionsgleichung von HRID 236023
Cl.CS[C:4]1[NH:5][CH2:6][C:7]([CH3:10])([CH3:9])[N:8]=1.[CH3:11][CH:12]([CH3:15])[CH2:13][NH2:14].ClC1C=CC(CN)=CC=1.[N:25](=[C:27]([C:33]#[N:34])[C:28](OCC)=[O:29])[OH:26].S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>C(O)=O>[NH2:34][C:33]1[N:14]([CH2:13][CH:12]([CH3:15])[CH3:11])[C:4]2[N:5]([CH2:6][C:7]([CH3:10])([CH3:9])[N:8]=2)[C:28](=[O:29])[C:27]=1[N:25]=[O:26]

Komponenten

8

Edukt 6

HCID 6558IsobutylamineHCID 14798Sodium HydroxideHCID 660364-ChlorobenzylamineHCID 146045Sodium dithionateHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateHCID 1785034432-Methylthio-4,4-dimethyl-2-imidazoline hydrochloride

Produkt 1

HCID 1784484247-amino-2,2-dimethyl-8-(2-methylpropyl)-6-nitroso-3H-imidazo[1,2-a]pyrimidin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

7-Amino-2,3-dihydro-2,2-dimethyl-8-(2-methylpropyl)-6-nitrosoimidazo[1,2-a]pyrimidin-5(8H)-one was prepared by reaction of the 2-methylthio-4,4-dimethyl-2-imidazoline hydrochloride with 2-methylpropylamine according to the method of Procedure 103 by substitution of the latter for p-chlorobenzylamine. The reaction product from this step was then condensed with ethyl oximinocyanoacetate as described in Procedure 103. The resulting nitroso compound was then reduced with sodium dithionate in formic acid and the resulting formylamino compound was cyclized with dilute aqueous sodium hydroxide according to Procedure 100.

Quellen und Nachweise

ORD-Eintrag
ord-34390cdd680c49d5b7b53b91fe295eb9
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04642345

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