6-Chloroguanine

Description

2-Amino-6-chloropurine is a precursor in the synthesis of nucleoside analogs with antiviral activity against Epstein-Barr virus (EBV) and human herpes virus 6 (HHV-6).

Chemical properties

white to light yellow crystal powder

The Uses of 6-Chloroguanine

2-Amino-6-chloropurine finds its uses in the enzymatic synthesis of 2?-deoxyguanosine, 9-alkyl purines and (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases.

The Uses of 6-Chloroguanine

2-Amino-6-chloropurine may be used:

• in the enzymatic synthesis of 2′-deoxyguanosine
• in the synthesis of 9-alkyl purines
• in the synthesis of (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases

Definition

ChEBI: 6-chloroguanine is an organochlorine compound that is 7H-purin-2-amine substituted by a chloro group at position 6. It is a member of 2-aminopurines and an organochlorine compound.

General Description

2-Amino-6-chloropurine is a 6-substituted purine. Tautomeric purine forms of 2-amino-6-chloropurine were investigated by vibrational spectroscopy and quantum chemical method.

Synthesis

Preparation of 2-amino-6-chloropurine:
Diacetyl guanine (8.0g, 0.034 moles), triethyimethylammonium chloride (15.45g, 0.102 moles), and triethylamine (4.74 mis, 0.034 moles) were heated together with stirring in acetonitrile (70mls) to 50°C. Phosphorus oxychioride (6.34 mis, 0.068 moles) was then added and stirring continued for 4 hours. The reaction mixture was cooled and then added to aqueous sodium hydroxide solution (20g in 300mls water). The reaction mixture was heated to 80°C for 2 hours and then the volume made up to 300 mis with water. The mixture was cooled to 25°C and the pH adjuster to 7 using 10% hydrochloric acid. The resulting slurry was stirred for fifteen minutes and the product filtered off and washed with water 30 mis and then dried at 80°C under vacuum to give a cream/off white coloured product, 2-amino-6-chioropurine 4.69 g (74.6% yield).