Реакция #2075734

Уравнение реакции

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

Выход 67.0%

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

Выход 67.0%

Условия реакции

Обработка

1. 1
   Другоеdry
2. 2
   Температураheated to reflux
3. 3
   Температураthe mixture was cooled
4. 4
   workup.ADDITIONmixed with ethyl acetate and water
5. 5
   ПромывкаThe organic phase was washed with water, brine
6. 6
   Другоеdried
7. 7
   Другоеevaporated under vacuum
8. 8
   ДругоеThe residue was purified by flash chromatography on silica gel with 20% ethyl acetaete/hexane

Методика

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).

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