反応 #6623

反応方程式

2-(2-propynyloxy)-tetrahydropyran

3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine

2-(2-propynyloxy)-tetrahydropyran

triphenyl phosphine

triethyl amine

→

3-(3-tetrahydropyr-2-yloxyprop-1-yn-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度is heated
2. 2
   温度at reflux under nitrogen for 12 hours
3. 3
   温度reflux
4. 4
   温度After heating for a total of 24 hours
5. 5
   温度under reflux
6. 6
   その他the solvent is removed under reduced pressure
7. 7
   ろ過the residue filtered through silica gel using 2% methanol in methylene chloride
8. 8
   濃縮This filtrate is concentrated
9. 9
   その他chromatographed on silica gel eluting with 20:1 ethyl acetate

実験手順

A mixture of 14.6 g of 3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 7.6 g of 2-(2-propynyloxy)-tetrahydropyran, 798 mg (10%) of palladium chloride, 2.36 g (20%) of triphenyl phosphine, 428 mg (5%) of cuprous iodide, 45 ml of triethyl amine and 700 ml of acetonitrile is heated at reflux under nitrogen for 12 hours. There then are added to the hot reaction mixture 3.2 g of 2-(2-propynyloxy)-tetrahydropyran and reflux is continued for an additional 12 hours. After heating for a total of 24 hours under reflux, the solvent is removed under reduced pressure, and the residue filtered through silica gel using 2% methanol in methylene chloride. This filtrate is concentrated and chromatographed on silica gel eluting with 20:1 ethyl acetate:hexane mixture to give 3-(3-tetrahydropyr-2-yloxyprop-1-yn-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine which is further purified by recrystallization with ethyl acetate.

出典