Réaction #2075730

Équation de réaction

6-Chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethoxy-pyrimidine-4-carboxylic acid

ammonium hydroxide

hydrochloric acid

hydrochloric acid

→

title compound

Rendement 69.0%

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethoxy-pyrimidine-4-carboxylic acid

Rendement 69.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was sealed
2. 2
   ExtractionThe product was then extracted with dichloromethane five times
3. 3
   AutreThe combined organic layers were then dried
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Mode opératoire

6-Chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethoxy-pyrimidine-4-carboxylic acid (380 mg, 1.1 mmol) was slurried in water (3.5 mL) and 28% aqueous ammonium hydroxide solution (720 μL, 10.6 mmol) was added. The reaction mixture was sealed and heated at 80° C. for 24 h. The reaction mixture was then acidified to pH 7 via dropwise addition of concentrated hydrochloric acid, and the crude product transferred into a 500 mL separatory funnel containing 100 mL 0.1M hydrochloric acid solution. The product was then extracted with dichloromethane five times. The combined organic layers were then dried, filtered and concentrated to yield the title compound (250 mg, 69% yield) as a tan solid: 1H NMR (DMSO-d6) δ 7.58 (dd, 1H, J=8, 9 Hz), 7.38 (dd, 1H, J=2, 9 Hz), 3.98 (q, 2H, J=7 Hz), 3.90 (d, 3H, J=1 Hz), 1.31 (t, 3H, J=7 Hz).

Source