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

HRID 431237Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[C:12](C(F)(F)F)[CH:11]=2)[N:5]=[C:4]([N:20]2[CH2:29][CH2:28][C:27]3[C:22](=CC=CC=3)C2)[CH:3]=1.[Cl:30]C1C=C(C)N=C(C=CC2C=CC=C(Cl)C=2)N=1.N1CCCC1>C(Cl)Cl.CCOC(C)=O>[Cl:30][C:12]1[CH:11]=[C:10](/[CH:9]=[CH:8]/[C:6]2[N:7]=[C:2]([CH3:1])[CH:3]=[C:4]([N:20]3[CH2:29][CH2:28][CH2:27][CH2:22]3)[N:5]=2)[CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

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).

Workup

customThe excess pyrrolidine was removed in vacuo
customthe residue was purified on a silica gel chromatography column (eluted with CH2Cl2/EtOAc: 4/1)
customevacuated in vacuo
customthe solid residue was triturated with ether
filtrationfiltered off by suction

Sources & evidence

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

Reaction notes

Loading…