Reaction #985280

Reaction equation

5-amino-4,6-dichloropyrimidine

Et3N

neopentylamine

→

6-chloro-5-amino-4-(neopentylamino)-pyrimidine

Solvents

nBuOH

Conditions

Workup

1. 1
   Otherthe cooled reaction mixture
2. 2
   Otherwas evaporated under vacuum
3. 3
   Otherthe residue was chromatographed

Procedure

A solution of 5-amino-4,6-dichloropyrimidine (1 mmol) in nBuOH was treated with Et3N (1.2 mmol) and neopentylamine (1.05 mmol) at 80° C. After 12 h, the cooled reaction mixture was evaporated under vacuum and the residue was chromatographed to give 6-chloro-5-amino-4-(neopentylamino)-pyrimidine as a yellow solid. Step B. The 6-chloro-5-amino-4-(2-neopentylamino)pyrimidine (1 mmol) in DMSO was treated with 5-diethylphosphono-2-furaldehyde (1.5 mmol) and FeCl3-silica (2.0 mmol) at 80° C. for 12 h. The cooled reaction mixture was filtered and the filtrate was evaporated under vacuum. Chromatography afforded 6-chloro-N9-neopentyl-8-(2-(5-diethyl-phosphono)furanyl)purine as a yellow solid. Step C. 6-Chloro-N9-neopentyl-8-(2-(5-diethylphosphono)furanyl)purine (1 mmol) in THF-DMSO was treated with liquid ammonia (2 mL) in a steel bomb. After 12 h, the reaction was evaporated under vacuum and the residue was purified through chromatography to give N9-neopentyl-8-(2-(5-diethylphosphono)furanyl)adenine as a yellow solid. Step D. A solution of N9-neopentyl-8-(2-(5-diethylphosphono)furanyl)-adenine (1 mmol) in acetonitrile was treated with bromotrimethylsilane (10 mmol). After 12 h, the reaction was evaporated under vacuum and the residue was treated with a mixture of water and acetonitrile. The solid was collected through filtration.

Source