Reaction #1109079

Reaction equation

Cyclopropylcarbamidine hydrochloride

triethylamine

2-chloroacrylo-nitrile

→

196a

Yield 27.0%

2-cyclopropylpyrimidin-4-amine

Yield 27.0%

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe resulting orange-yellow solution was refluxed for 1 h
2. 2
   Filtrationfiltered
3. 3
   ConcentrationThe filtrate was concentrated in vacuo
4. 4
   Otherthe residue was purified by reverse-phase Combiflash

Procedure

Cyclopropylcarbamidine hydrochloride (1.0 g, 8.3 mmol) was dissolved in ethanol (25 mL) and triethylamine (1.26 g, 12.5 mmol), followed by the addition of 2-chloroacrylo-nitrile (870 mg, 10 mmol). The resulting orange-yellow solution was refluxed for 1 h. The mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was purified by reverse-phase Combiflash to afford 196a (300 mg, 27%) as a light brown solid. MS-ESI: [M+H]+ 136

Source