Reaction #1265398

Reaction equation

2-amino-6-chloro-4-n-pentyloxypteridine

tri-o-tolylphosphane

styrene

triethylamine

→

orange powder

Yield 72.9%

2-amino-4-n-pentyloxy-6-styrylpteridine

Yield 72.9%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureunder reflux for 90 hours
2. 2
   OtherIt was evaporated
3. 3
   Otherthe residue purified by silica gel column chromatography with chloroform
4. 4
   OtherThe product fraction was evaporated

Procedure

A mixture of 1.5 g (5.6 mmoles) 2-amino-6-chloro-4-n-pentyloxypteridine (e.g. available following the procedure disclosed by Mohr et al. in Helv. Chem. Acta (1992) 75:2317), palladium acetate (63 mg, 0.28 mmoles), tri-o-tolylphosphane (682 mg, 2.24 mmoles), cuprous iodide (53 mg, 0.28 mmoles), styrene (1,3 ml., 11.3 mmoles) and triethylamine 3.1 ml, 22 mmoles) was stirred in dry acetonitrile (50 ml) under reflux for 90 hours. It was evaporated and the residue purified by silica gel column chromatography with chloroform. The product fraction was evaporated to give 1.37 g (yield: 72%) of an orange powder exhibiting, after recrystallization from a EtOAc/hexane mixture, a melting point (m.p.) range of 127–128° C.

Source