Sodium ethoxide → 5-Bromo-2-(propan-2-yl)pyrimidine-4-carboxylic acid

HRID 467621

Reaktionsgleichung

Cl.[C:2]([NH2:7])(=[NH:6])[CH:3]([CH3:5])[CH3:4].CC[O-].[Na+].[C:12]([OH:20])(=[O:19])/[C:13](=[C:15](\[CH:17]=O)/[Br:16])/Br>CCO>[Br:16][C:15]1[C:13]([C:12]([OH:20])=[O:19])=[N:6][C:2]([CH:3]([CH3:5])[CH3:4])=[N:7][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a stirred suspension of isobutyramidine hydrochloride (6.47 g, 47.5 mmol) at rt in EtOH (30 ml) under an argon atmosphere was added NaOEt solution (21 ml, 21% in EtOH) over min. The suspension was heated to 50° C. and a solution of mucobromic acid (5.7 g, 22.1 mmol) in EtOH (24 ml) was added dropwise over 5 min at 50° C. An additional portion of NaOEt solution (12 ml, 21% in EtOH) was added dropwise over 5 min. The mixture was then cooled to rt. The solids were filtered off, and the cake was washed with plenty of ethanol. The filtrate was concentrated to leave the crude product as a light brown solid. The crude material was triturated in 2 N HCl (100 ml). The product was collected by filtration, washed with plenty of H2O and plenty of n-heptane and dried to give the product (2.09 g, 73%) as beige solid.

Aufarbeitung

temperatureThe mixture was then cooled to rt
filtrationThe solids were filtered off
washthe cake was washed with plenty of ethanol
concentrationThe filtrate was concentrated
customto leave the crude product as a light brown solid
customThe crude material was triturated in 2 N HCl (100 ml)
filtrationThe product was collected by filtration
washwashed with plenty of H2O and plenty of n-heptane
customdried

Quellen und Nachweise

ORD-Eintrag: ord-032b09cd601f4788b77b27dbc9d302a2
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08623866B2

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