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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

수율 67.0%

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

수율 67.0%

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후처리

1. 1
   기타dry
2. 2
   온도heated to reflux
3. 3
   온도the mixture was cooled
4. 4
   workup.ADDITIONmixed with ethyl acetate and water
5. 5
   세척The organic phase was washed with water, brine
6. 6
   기타dried
7. 7
   기타evaporated under vacuum
8. 8
   기타The residue was purified by flash chromatography on silica gel with 20% ethyl acetaete/hexane

실험 절차

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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