تفاعل #2075734

معادلة التفاعل

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

المردود 67.0%

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

المردود 67.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىdry
2. 2
   درجة الحرارةheated to reflux
3. 3
   درجة الحرارةthe mixture was cooled
4. 4
   workup.ADDITIONmixed with ethyl acetate and water
5. 5
   غسيلThe organic phase was washed with water, brine
6. 6
   أخرىdried
7. 7
   أخرىevaporated under vacuum
8. 8
   أخرىThe residue was purified by flash chromatography on silica gel with 20% ethyl acetaete/hexane

الإجراء التجريبي

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).

المصدر