Reaktion #8712

Reaktionsgleichung

sodium hydride

2-phenyl-ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

2-chloro-pyrimidine

→

2-phenyl-ethanesulfonic acid {6-[2-(pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide

Ausbeute 74.6%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   SonstigeThe solvent was evaporated
3. 3
   workup.ADDITIONdiethylether (20 ml) was added to the residue
4. 4
   FiltrationThe precipitate was filtered off
5. 5
   Waschenwashed with diethylether
6. 6
   workup.DISSOLUTIONdissolved in water (20 ml)
7. 7
   Extraktionextracted twice with EA (50 ml)
8. 8
   WaschenThe organic phase was washed with water
9. 9
   Trocknendried over Na2SO4
10. 10
    Sonstigeevaporated
11. 11
    workup.STIRRINGstirred at 70° C. for 10 min
12. 12
    Sonstigeis collected
13. 13
    Waschenwashed with 2-propanol (2 ml)
14. 14
    Sonstigedried under high vacuum

Vorschrift

To sodium hydride (50 mg, 60% in mineral oil) was added THF (25 ml) followed by 2-phenyl-ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (150 mg, Referential Example 1). The mixture was stirred for 1 h at rt before 2-chloro-pyrimidine (86 mg) was added. Stirring was continued for 17 h at 80° C. The solvent was evaporated and diethylether (20 ml) was added to the residue. The precipitate was filtered off and washed with diethylether, dissolved in water (20 ml) and acidified with citric acid and extracted twice with EA (50 ml). The organic phase was washed with water, dried over Na2SO4 and evaporated. The residue is suspended in 2-propanol (15 ml) and stirred at 70° C. for 10 min and cooled to 0° C. before the solid material is collected, washed with 2-propanol (2 ml) and dried under high vacuum to furnish 2-phenyl-ethanesulfonic acid {6-[2-(pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide (133 mg) as a white powder. LC-MS: tR=4.97 min, [M+1]+=492.34, [M−1]−=490.28.

Quelle