Download (8Mb) - Etheses - Saurashtra University

4.7 Experimental protocols
4.7.1 General Procedure for the Preparation 3-Azido-propylamine
To a solution of 3-chloropropan-1-amine hydrochloride (3.2 g, 14.6 mmol) in water
(10 mL) was slowly added NaN3 (3.2 g, 49.2 mmol) as a solution in water (15 mL).
The resulting solution was allowed to stir at reflux overnight. After cooling to room
temperature, about 2/3 of the water was removed by evaporation and the remaining
residue diluted with ether (50 mL). This biphasic mixture was cooled to 0 °C and
KOH pellets (4.0 g) were slowly added. The phases separated and the aqueous layer
extracted with ether (2 x 30 mL). All organics combined, dried over Na2SO4, and
concentrated to afford 3-Azido-propylamine (1.17 g, 80%) as yellow oil
4.7.2 General Procedure for the Preparation of N-(3-azidopropyl)pyrimidin-2amine:
In a 50 mL microwave vial were successively dissolved in EtOH (20 mL) 2chloropyrimidine
(3.43 g, 30 mmol), 3-Azido-propylamine (48 mmol, 1.6 equiv) and
triethylamine (6.2 mL, 45 mmol, 1.5 equiv). The reaction tube was sealed, and
irradiated in the cavity of a Milestone MicroSYNTH microwave reactor at a ceiling
temperature of 120 °C at 100 W maximum power for 60 min. After the reaction
mixture was cooled with an air flow for 15 min, it was diluted with water (100 mL),
extracted with DCM (2×150 mL) and dried over Na2SO4. The solvent was evaporated
in vaccuo, and the crude mixture was purified by silica gel flash chromatography
using 0-5% MeOH−DCM as the eluent.
4.7.3 General Procedure for the Preparation of Salts.
To a solution of N-(3-azidopropyl)pyrimidin-2-amine (6 mmol) and αbromoacetophenone
(7.2 mmol, 1.2 equiv) in acetonitrile (12 mL) was added 4dimethylaminopyridine
(6 mg, 0.05 mmol). After being stirred at 85 °C for 5 h, the
reaction mixture was diluted with acetone (20 mL) and the precipitate was filtered and
washed with acetone (2×20 mL), ether (2×20 mL) and dried over P2O5 to give salt as
a white solid.