Reaktion #162208

Reaktionsgleichung

2,4-dichloro-5-fluoro-pyrimidine

66d

racemic methyl-3-amino-2-hydroxy-1-methyl-cyclohexanecarboxylate

iPr2NEt

→

racemic methyl-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]-2-hydroxy-1-methyl-cyclohexanecarboxylate

Ausbeute 87.0%

Lösungsmittel

THF

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction overnight at room temperature
2. 2
   Sonstigethe solvent was evaporated under reduced pressure
3. 3
   Sonstigethe crude residue was purified by silica gel chromatography (Hexanes/EtOAc 100/0 to 0/100, Rf=0.7 in Hexanes/EtOAc 2/1)

Vorschrift

To a solution of 2,4-dichloro-5-fluoro-pyrimidine (0.43 g, 2.58 mmol) and racemic methyl-3-amino-2-hydroxy-1-methyl-cyclohexanecarboxylate acetic acid salt, 66d, (0.58 g, 2.35 mmol) in THF (10 mL) and MeOH (8 mL) at room temperature was added iPr2NEt (1.23 mL, 7.04 mmol). After stirring the reaction overnight at room temperature, the solvent was evaporated under reduced pressure and the crude residue was purified by silica gel chromatography (Hexanes/EtOAc 100/0 to 0/100, Rf=0.7 in Hexanes/EtOAc 2/1) to provide 650 mg of racemic methyl-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]-2-hydroxy-1-methyl-cyclohexanecarboxylate, 66e, as a white solid. LCMS: 318.16 (M+1).

Quelle