Reaktion #1102267

Reaktionsgleichung

7-Methoxy-1-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ol

6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

TBTU

acetonitrile

→

title compound

Ausbeute 21.1%

(6-Bromo-pyrazolo[1,5-a]pyrimidin-2-yl)-(6-hydroxy-7-methoxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl)-methanone

Ausbeute 21.1%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat room temperature for 8 h
2. 2
   Einengenconcentrated
3. 3
   ExtraktionThe residue is extracted with dichloromethane
4. 4
   WaschenThe extract is washed with water (20 ml)
5. 5
   Trocknendried over sodium disulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue is purified by column chromatography on silica gel (eluent: hexane/ethyl acetate—1/1, Rf 0.3)

Vorschrift

To a solution of 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (1.4 g, 5.8 mmol, 1.0 equiv) and TBTU (2.0 g, 6.2 mmol, 1.1 equiv) in dry acetonitrile (30 mL) triethylamine (2 mL, 14.5 mmol, 2.5 equiv) is added. 7-Methoxy-1-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ol (1.4 g, 7.25 mmol, 1.25 equiv) is then added. The reaction mixture is stirred at 50° C. for 2 h, then at room temperature for 8 h, and concentrated. The residue is extracted with dichloromethane. The extract is washed with water (20 ml), dried over sodium disulfate, and concentrated. The residue is purified by column chromatography on silica gel (eluent: hexane/ethyl acetate—1/1, Rf 0.3) to provide 0.511 g of the title compound as an oil.

Quelle