Reaktion #816837

Reaktionsgleichung

imidazole

subtitle product

6-Chloro-2-[(3-chloro-2-fluorobenzyl)thio]pyrimidin-4-amine

tert-butyldimethylsilyl chloride

N,N-Diisopropylethylamine

(R)-alaninol

→

subtitle compound

N-((1R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-[(3-chloro-2-fluoro-benzyl)thio]pyrimidine-4,6-diamine

Lösungsmittel

NMP

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintained for 1 h
2. 2
   SonstigeThe volatiles were removed in vacuo
3. 3
   Sonstigethe residue was purified by column chromatography (1:1 Et2O/iso-hexane)

Vorschrift

N,N-Diisopropylethylamine (5.2 ml) was added to a solution of (R)-alaninol (2.56 ml) and the subtitle product of step ii) in NMP (35 ml) and stirred at 100° C. for 24 h and then 140° C. for 24 h. After cooling to ambient temperature imidazole (2.60 g) and a solution of tert-butyldimethylsilyl chloride (2.60 g) in THF (10 ml) were added and stirring maintained for 1 h. The volatiles were removed in vacuo and the residue was purified by column chromatography (1:1 Et2O/iso-hexane) to afford the subtitle compound as a yellow oil. Yield: 1.70 g.

Quelle