Reaction #56907

Reaction equation

2-(2-amino-6-chloro-pyrimidin-4-yl)-4-bromo-phenol

1-propanol

triphenylphosphine

diethyl azodicarboxylate

→

4-(5-bromo-2-propoxy-phenyl)-6-chloro-pyrimidin-2-ylamine

Yield 52.5%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Concentrationthe mixture was concentrated under reduced pressure
2. 2
   OtherThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:6)

Procedure

To the stirred solution of 2-(2-amino-6-chloro-pyrimidin-4-yl)-4-bromo-phenol (0.060 g, 0.20 mmol), 1-propanol (0.036 g, 0.60 mmol), and triphenylphosphine (0.157 g, 0.60 mmol) in tetrahydrofuran (5.0 ml) was added diethyl azodicarboxylate (0.104 g, 0.60 mmol). After stirring for 16 hours, the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:6) to provide 4-(5-bromo-2-propoxy-phenyl)-6-chloro-pyrimidin-2-ylamine (0.036 g, 52% yield) as a white powder.

Source