Pivalaldehyde → HCID 13072124, Verbindung

HRID 1903564Notizen

Reaktionsgleichung

Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.C([Li])CCC.[CH3:13][C:14]([CH3:18])([CH3:17])[CH:15]=[O:16].[Cl-].[NH4+]>O1CCCC1.CCOCC.O>[OH:16][CH:15]([C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1)[C:14]([CH3:18])([CH3:17])[CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: -120 °C

Versuchsvorschrift

225 g of 5-bromopyrimidine were dissolved in 1.5 liters of absolute tetrahydrofuran/1,000 ml of absolute ether, and the solution was cooled to -120° C. 250 ml of 50% strength n-butyl-lithium (in n-hexane) were added dropwise to the solution, during the course of 2 hours, at an internal temperature of -105° to -115° C. The mixture was further stirred for 1 hour at this temperature. 309 ml of trimethylacetaldehyde was then added dropwise during the course of 2 hours. The reaction mixture was then further stirred for 4 hours at this temperature. The reaction mixture was allowed to warm up to room temperature overnight, and 83 g of ammonium chloride, dissolved in a minimum quantity of water, were then added to it. The aqueous phase was separated off, and the organic phase was washed twice with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated. 155 g (56% of theory) of 5-(1-hydroxy-2,2 -dimethylpropyl)pyrimidine of melting point 94°-96° C. were obtained after recrystallization of the residue from acetonitrile.

Aufarbeitung

stirringThe reaction mixture was then further stirred for 4 hours at this temperature
temperatureto warm up to room temperature overnight
additionwere then added to it
customThe aqueous phase was separated off
washthe organic phase was washed twice with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulphate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-8d323af6b9f8436eaf117fcee0774ad7
Quelldatensatz: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04436907

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