Reaktion #69169

Reaktionsgleichung

4-chloro-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

DMF

potassium carbonate

→

4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

Lösungsmittel

ethyl acetate

Water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was purged with a steady stream of nitrogen for 15 minutes
2. 2
   Temperaturto cool
3. 3
   SonstigeThe diluted reaction mixture
4. 4
   Waschenwas washed with water, brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto give a solution in a small volume of DMF (about 2-3 mL)
8. 8
   Sonstigeto form a gum on the walls of the flask
9. 9
   SonstigeThen water was decanted
10. 10
    workup.DISSOLUTIONthe solids were dissolved in ethyl acetate
11. 11
    TrocknenThe solution was dried over Na2SO4
12. 12
    Einengenconcentrated in vacuo
13. 13
    Sonstigeto afford a yellow solid
14. 14
    SonstigeThe product was triturated with ethyl ether

Vorschrift

To a mixture of 4-chloro-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (1.4 g, 0.0049 mol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.4 g, 0.0074 mol) in DMF (40 mL, 0.5 mol) was added potassium carbonate (2.0 g, 0.015 mol) in 15 mL of water. The mixture was purged with a steady stream of nitrogen for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.41 g, 0.00036 mol) was added and the reaction was heated to 125° C. for 30 min. The mixture was allowed to cool then diluted with ethyl acetate. The diluted reaction mixture was washed with water, brine, dried over Na2SO4 and concentrated to give a solution in a small volume of DMF (about 2-3 mL). Water was added, causing the material to form a gum on the walls of the flask. Then water was decanted, and the solids were dissolved in ethyl acetate. The solution was dried over Na2SO4, and concentrated in vacuo to afford a yellow solid. The product was triturated with ethyl ether to yield 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine as a white powder which was dried under vacuum (1 g, 60%). 1H NMR (300 MHz, CDCl3): δ □10.80 (br s, 1H), 8.93 (s, 1H), 8.46 (s, 2H), 7.46 (d, 1H), 6.88 (d, 1H), 5.73 (s, 2H), 3.61 (dd, 2H), 0.98 (dd, 2H), 0.00 (s, 9H); MS (ES): 316 (M+1).

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