Reaction #84652

Reaction equation

2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline

tert-butyl ((1S,2R)-2-aminocyclohexyl)carbamate

DBU

→

tert-butyl ((1S,2R)-2-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclohexyl)carbamate

Yield 81.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherwas degassed with N2 for 5 mins
2. 2
   TemperatureThe mixture was cooled to room temperature
3. 3
   Concentrationconcentrated
4. 4
   Otherthe residue was purified by silica gel column chromatography

Procedure

A mixture of 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline (0.95 g, 2.6 mmol), tert-butyl ((1S,2R)-2-aminocyclohexyl)carbamate (1.1 g, 5.14 mmol), and DBU (0.77 mL, 5.14 mmol) in acetonitrile (9 mL) was degassed with N2 for 5 mins and heated at 70° C. for 16 h. The mixture was cooled to room temperature, concentrated and the residue was purified by silica gel column chromatography to afford tert-butyl ((1S,2R)-2-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclohexyl)carbamate (1.1 g, 81%). MS (ES+) C27H32Cl2N4O4 requires: 546, found: 547 [M+H]+.

Source