Reaction #8826

Reaction equation

1,2,3,4-tetrahydro-isoquinolin-5-ylamine

2-chloro-6,7-dimethoxy-3H-quinazolin-4-one

→

2-(5-amino-3,4-dihydro-1H-isoquinolin-2-yl)-6,7-dimethoxy-3H-quinazolin-4-one

Yield 49.7%

Solvents

methoxyethanol

Conditions

Workup

1. 1
   OtherThe volatiles were evaporated
2. 2
   Otherthe residue was purified by flash column chromatography
3. 3
   Washeluting with 3% methanol in dichloromethane containing 0.3% of ammonium hydroxide

Procedure

A mixture of 1,2,3,4-tetrahydro-isoquinolin-5-ylamine 24a (3.83 g, 25.84 mmol) and 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b (5.9 g, 24.54 mmol) in methoxyethanol (60 mL) was heated to 60° C. with stirring for 48 h. The volatiles were evaporated and the residue was purified by flash column chromatography eluting with 3% methanol in dichloromethane containing 0.3% of ammonium hydroxide to yield 4.3 g of 2-(5-amino-3,4-dihydro-1H-isoquinolin-2-yl)-6,7-dimethoxy-3H-quinazolin-4-one 110.

Source