Cyclopentylamine → 2-chloro-N-cyclopentyl-5-nitropyrimidin-4-amine

Participants

Reaction Steps

To a solution of 5.82 g (30 mmol) of 2,4-dichloro-5-nitropyrimidine (N. Whittaker, J. Chem. Soc., 1951:1565–1570) in 100 mL THF at −78° C. is added dropwise over 5 minutes a solution of 5.11 g (60 mmol) of cyclopentylamine in 20 mL THF. After a further 10 minutes at −78° C., the mixture is allowed to warm to room temperature, and the solvent is removed under vacuum. The residue is then extracted into EtOAc, washed with water, and dried with Na2SO4. Removal of the solvent and chromatography on SiO2, eluting with hexane/EtOAc (95:5) gives 6.20 g (85%) of the title compound: mp (hexane) 80–81.5° C.

Provenance & Evidence