Ethylenediamine → N-(5-pyrimidinylmethyl)ethylenediamine

Ethylenediamine (60 g) was dissolved in benzene (200 ml), and 5-formylpyrimidine (21.6 g) was added at room temperature. Subsequently, the mixture was heated, and refluxed for 3 hours while removing water as an azeotrope. After the reaction, benzene and the excess of ethylenediamine were distilled off under reduced pressure. The residue was dissolved in ethanol (200 ml). Sodium borohydride. (8.4 g) was added portionwise to this solution at room temperature, and subsequently the mixture was stirred at room temperature for 5 hours. Ethanol was distilled off under reduced pressure. Dichloromethane (100 ml) was added to the residue, and a dichloromethane-soluble portion was separated. Dichloromethane was distilled off from the dichloromethane layer under reduced pressure to give N-(5-pyrimidinylmethyl)-ethylenediamine (25.8 g) as a colorless oil. nD25=1.5532.

1. temperatureSubsequently, the mixture was heated
2. temperaturerefluxed for 3 hours
3. customwhile removing water as an azeotrope
4. customAfter the reaction, benzene
5. distillationthe excess of ethylenediamine were distilled off under reduced pressure
6. dissolutionThe residue was dissolved in ethanol (200 ml)
7. addition(8.4 g) was added portionwise to this solution at room temperature
8. distillationEthanol was distilled off under reduced pressure
9. additionDichloromethane (100 ml) was added to the residue
10. customa dichloromethane-soluble portion was separated
11. distillationDichloromethane was distilled off from the dichloromethane layer under reduced pressure

ORD record

ord-971c2b7026634e6da822bfff4940f186

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06297374B1