Ammonium Hydroxide → HCID 12971789, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N2-(2-Ethoxypyridin-5-yl)guanine (6.35 g; 23.3 mmol) and N,N-dimethylformamide (70 mL) is cooled to 0° C. and treated dropwise with thionyl chloride (5.6 mL; 76.8 mmol). An additional 15 ml of N,N-dimethylformamide is added and the mixture is heated at 50° C. for 1 h. The reaction mixture is cooled to room temperature and poured slowly into a solution of sodium bicarbonate (8 g) in water (80 mL). The pH is adjusted to 6 with saturated aqueous sodium bicarbonate solution and the mixture is chilled overnight. The precipitate is collected by filtration and washed with water and methanol to give a brown solid which is dissolved in warm concentrated ammonium hydroxide (30 mL) and allowed to stand at room temperature for 3 days. The precipitate is collected by filtration and washed with water and methanol to afford 2-[(2-Ethoxypyrid-5-yl)amino]-6-chloropurine (4.72 g).

Provenance & Evidence