Reaktion #44707

Reaktionsgleichung

N,N-diisopropylethylamine

benzyl 3-(2-amino-6-hydroxypyrimidin-4-yl)piperidine-1-carboxylate

sodium hydroxide

phosphoryl chloride

→

Benzyl 3-(2-amino-6-chloropyrimidin-4-yl)piperidine-1-carboxylate

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturFor work-up, the reaction solution is cooled to 0° C.
2. 2
   Extraktionextracted three times with ethyl acetate (in each case 70 ml)
3. 3
   TrocknenThe organic phase is dried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue is purified on a silica gel column

Vorschrift

4.14 g (12.60 mmol) of benzyl 3-(2-amino-6-hydroxypyrimidin-4-yl)piperidine-1-carboxylate (from example LXXI) are suspended in 150 ml of acetonitrile. 3.29 ml (18.91 mmol) of N,N-diisopropylethylamine and 0.57 g (2.52 mmol) of benzyltriethylammonium chloride are added successively. The mixture is cooled to 0° C. At 0° C., 4.7 ml (50.43 mmol) of phosphoryl chloride are then slowly added dropwise. The mixture is stirred at room temperature for 18 hours. For work-up, the reaction solution is cooled to 0° C. and carefully added dropwise to ice water (150 ml). The aqueous suspension is neutralized using a 45% strength sodium hydroxide solution and extracted three times with ethyl acetate (in each case 70 ml). The organic phase is dried over anhydrous magnesium sulfate and concentrated. The residue is purified on a silica gel column using dichloromethane/methanol 30:1. This gives 2.80 g (64% of theory) of product.

Quelle