Pyrrolidine → (E)-2-[2-(3-Chloro-phenyl)-vinyl]-4-methyl-6-pyrrolidin-1-yl-pyrimidine

Participants

Role	Name	HCID	Charge
Reactant	Pyrrolidine	HCID 31268	—
Reactant	(E)-2-{6-methyl-2-[2-(3-trifluoromethyl-phenyl)-vinyl]-pyrimidin-4-yl}-1,2,3,4-tetrahydro-isoquinoline	HCID 18763632	—
Reactant	4-Chloro-2-[2-(3-chloro-phenyl)-vinyl]-6-methyl-pyrimidine	HCID 73462185	—
Solvent	Dichloromethane ethylacetate	HCID 21226138	—
Product	(E)-2-[2-(3-Chloro-phenyl)-vinyl]-4-methyl-6-pyrrolidin-1-yl-pyrimidine	HCID 9835946	80%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of 66 mg (0.25 mmol) of (E) 4-chloro-2-[2-(3-chloro-phenyl)-vinyl]-6-methyl-pyrimidine and 0.89 g (12.5 mmol) pyrrolidine was heated at 60° C. for 1.5 h after which time the reaction was completed according to TLC analysis (CH2Cl2/EtOAc: 4/1). The excess pyrrolidine was removed in vacuo and the residue was purified on a silica gel chromatography column (eluted with CH2Cl2/EtOAc: 4/1). The purified fractions were combined, evacuated in vacuo, the solid residue was triturated with ether and filtered off by suction to give (E)-2-[2-(3-Chloro-phenyl)-vinyl]-4-methyl-6-pyrrolidin-1-yl-pyrimidine (61 mg, 80%) as an off-white crystalline solid. ISP mass spectrum, m/e: 300.3 (M+1 calculated for C17H18ClN3: 300).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06657060B2
Source dataset	uspto-grants-2003_12
ORD ID	ord-af9e1104b7c1445bb08a23a6a174d4bc
Source note	uspto-grants-2003_12