N,N-Dimethylaniline → 2-[[4-[4-(Tert-butoxycarbonyl)piperazin-1-yl]phenyl]-amino]-4-(cyclopentylamino)-5-nitropyrimidine

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethylaniline	HCID 949	—
Reactant	2-chloro-N-cyclopentyl-5-nitropyrimidin-4-amine	HCID 7147253	—
Reactant	tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate	HCID 11011301	—
Solvent	Acetic Acid	HCID 176	—
Solvent	Water	HCID 962	—
Solvent	Isopropanol	HCID 3776	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-[[4-[4-(Tert-butoxycarbonyl)piperazin-1-yl]phenyl]-amino]-4-(cyclopentylamino)-5-nitropyrimidine	HCID 58786785	94.4%

Reaction Steps

To a solution of 0.73 g (3 mmol) of 2-chloro-4-(cyclopentylamino)-5-nitropyrimidine and 0.49 g (4 mmol) N,N-dimethylaniline in 10 mL THF is added a solution of 0.94 g (3.4 mmol) of 1-(tert-butoxycarbonyl)-4-(4-aminophenyl)-piperazine in 20 mL of 2-propanol, and the resulting mixture is heated under reflux for 2 hours. After cooling and acidification with acetic acid, the mixture is diluted with water to give 1.37 g (94%) of the title compound: mp (MeOH) 194–196° C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07169778B2
Source dataset	uspto-grants-2007_01
ORD ID	ord-1980bb5f90eb4eaa9d824068aa3e4ffe
Source note	uspto-grants-2007_01