Reaktion #8328

Reaktionsgleichung

7-(3-Chloro-propoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

2-mercaptopyrimidine

potassium iodide

→

desired product

Ausbeute 76.0%

4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-7-[3-(pyrimidin-2-ylsulfanyl)-propoxy]-quinoline

Ausbeute 76.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe resin is washed sequentially with 9:1 dichloromethane
2. 2
   SonstigeThe ammonia washes are evaporated to dryness

Vorschrift

7-(3-Chloro-propoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (0.060 g, 0.148 mmol), 2-mercaptopyrimidine (0.033 g, 0.296 mmol, 2.0 equiv) and potassium iodide (0.010 g, 0.120 mmol, 0.80 equiv) are combined in N,N-dimethylformamide (1.0 mL) and the reaction is heated at 60° C. for 72 h. The mixture is placed on a 10 g SCX resin column. The resin is washed sequentially with 9:1 dichloromethane: methanol (2×120 mL), 4:1 dichloromethane: methanol (2 N ammonia) (2×125 mL), and methanol (2 N ammonia) (125 mL). The ammonia washes are evaporated to dryness and the residue is subjected to chromatography on silica gel (20 g, 99:1 dichloromethane: methanol (2 N ammonia)) to yield 0.054 g (76%) of the desired product as a tan solid.

Quelle