Reaktion #168867

Reaktionsgleichung

2-amino-4,6-dichloropyrimidine-5-carboaldehyde

Indium

sodium iodide

allyl bromide

→

title compound

1-(2-Amino-4,6-dichloropyrimidin-5-yl)-3-buten-1-ol

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThereafter, the reaction mixture was filtered through celite, and ethyl acetate
2. 2
   workup.ADDITIONwas then added to the filtrate
3. 3
   WaschenThe resulting mixture was successively washed with 1 N hydrochloric acid
4. 4
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Einengenwas then concentrated
6. 6
   workup.ADDITIONThereafter, hexane was added to the residue
7. 7
   Filtrationa precipitate was then collected by filtration

Vorschrift

Indium powder (0.23 g) and zinc powder (1.31 g) were added to a mixture composed of commercially available 2-amino-4,6-dichloropyrimidine-5-carboaldehyde (1.92 g) and N,N-dimethylformamide (20 ml). Thereafter, sodium iodide (0.15 g) and allyl bromide (1.73 ml) were added to the mixture at room temperature. The resulting mixture was stirred for 3 hours. Thereafter, the reaction mixture was filtered through celite, and ethyl acetate was then added to the filtrate. The resulting mixture was successively washed with 1 N hydrochloric acid and a saturated saline in this order. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated. Thereafter, hexane was added to the residue, and a precipitate was then collected by filtration, so as to obtain the above title compound (1.75 g) as a solid.

Quelle