Réaction #2075734

Équation de réaction

2-Chloro-6-methoxy-7-methyl-7H-purine

2-(4-chloro-2-fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

cesium fluoride

→

title compound

Rendement 67.0%

2-(4-Chloro-2-fluoro-3-methoxyphenyl)-6-methoxy-7-methyl-7H-purine

Rendement 67.0%

Conditions de réaction

Traitement

1. 1
   Autredry
2. 2
   Températureheated to reflux
3. 3
   Températurethe mixture was cooled
4. 4
   workup.ADDITIONmixed with ethyl acetate and water
5. 5
   LavageThe organic phase was washed with water, brine
6. 6
   Autredried
7. 7
   Autreevaporated under vacuum
8. 8
   AutreThe residue was purified by flash chromatography on silica gel with 20% ethyl acetaete/hexane

Mode opératoire

2-Chloro-6-methoxy-7-methyl-7H-purine (1.2 g, 6.0 mmol, see Monatshefte fuer Chemie (1985), 116(3), 341-51 for preparation), 2-(4-chloro-2-fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2.1 g, 8.6 mmol), Pd(PPh3)2Cl2 (300 mg, 0.42 mmol) and cesium fluoride (1.6 g, 11 mmol) were combined in 10 mL dry, deaerated acetonitrile and heated to reflux. After 2 h, the mixture was cooled and mixed with ethyl acetate and water. The organic phase was washed with water, brine, dried and evaporated under vacuum. The residue was purified by flash chromatography on silica gel with 20% ethyl acetaete/hexane to give the title compound (1.3 g, 67% yield: mp 191-192° C.: 1H NMR (CDCl3) δ 8.0 (s, 1H), 7.90 (dd, 1H), 7.22 (dd, 1H), 4.22 (s, 3H), 4.08 (s, 3H), 4.02 (s, 3H).

Source