Reaktion #168863

Reaktionsgleichung

pyridin-2-amine

4-chloroquinazolin-6-ylacetate

cesium carbonate

→

4-(pyridin-2-ylamino)quinazolin-6-ol

Ausbeute 64.4%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction liquid
2. 2
   Filtrationwas filtered
3. 3
   Extraktionextracted with chloroform
4. 4
   Waschenthe combined organic layers were washed with water
5. 5
   Trocknena saturated saline solution and dried over anhydrous sodium sulfate
6. 6
   Einengenby being concentrated under reduced pressure
7. 7
   workup.DISSOLUTIONThe resultant residue was dissolved in ammonia water (1 ml)
8. 8
   workup.STIRRINGmethanol (4 ml), and the solution was stirred at 50° C. for 2 hours
9. 9
   TemperaturThe reaction solution was cooled to room temperature
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    Sonstigethe precipitate was obtained through filtration
12. 12
    Waschenwashed with ether
13. 13
    Sonstigedried

Vorschrift

To a solution of pyridin-2-amine (101 mg, 1.08 mmol) and 4-chloroquinazolin-6-ylacetate (200 mg, 0.90 mmol) in toluene (4 ml), tris(dibenzylideneacetone)dipalladium (0) (82.0 mg, 0.090 mmol), (±)BINAP (112.0 mg, 0.180 mmol) and cesium carbonate (585 mg, 1.80 mmol) were added, and the mixture was stirred under nitrogen atmosphere at 120° C. for 2 hours. The reaction liquid was filtered, followed by vacuum concentration of the filtrate. The residue was suspended in water and then extracted with chloroform, and thereafter the combined organic layers were washed with water and a saturated saline solution and dried over anhydrous sodium sulfate, followed by being concentrated under reduced pressure. The resultant residue was dissolved in ammonia water (1 ml) and methanol (4 ml), and the solution was stirred at 50° C. for 2 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure, the resultant residue was suspended in ether, and the precipitate was obtained through filtration, washed with ether and then dried to give 4-(pyridin-2-ylamino)quinazolin-6-ol (138 mg, yield: 64%) as a brown solid.

Quelle