Reaktion #823499

Reaktionsgleichung

2,4-dichlorothieno[2,3-d]pyrimidine

NaH

4-hydroxy-3,5-dimethyl benzonitrile

→

product

Ausbeute 28.1%

4-(2-Chlorothieno[2,3-d]pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile

Ausbeute 28.1%

Lösungsmittel

THF

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated at 50° C. for 2 h
2. 2
   Waschenwashed with EtOAc
3. 3
   WaschenThe combined organic layers were washed with water, brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe crude product was purified by column chromatography
8. 8
   Wascheneluting with hexanes/ethyl acetate (5:1)

Vorschrift

A stirred suspension of NaH (85 mg, 2.12 mmol) in dry THF (12 mL) was added 4-hydroxy-3,5-dimethyl benzonitrile (311 mg, 2.12 mmol) and stirred at room temperature for 30 min under Argon. The reaction mixture was added to a solution of 2,4-dichlorothieno[2,3-d]pyrimidine (434 mg, 2.12 mmol) in dry THF (10 mL) and heated at 50° C. for 2 h, the resulting mixture was diluted with water and washed with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (5:1) to give the product as a white solid (188 mg, 28%):

Quelle