2,5-Dimethylpyrrolidine → 6-(2,5-Dimethylpyrrolidin-1-yl)pyridin-2-amine

HRID 1755339Notes

Reaction equation

F[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][CH:10]1[CH2:14][CH2:13][CH:12]([CH3:15])[NH:11]1>O>[CH3:9][CH:10]1[CH2:14][CH2:13][CH:12]([CH3:15])[N:11]1[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 205 °C

Procedure

A mixture of 6-fluoropyridin-2-amine (0.5 g, 4.46 mmol) and 2,5-dimethylpyrrolidine (0.664 g, 6.7 mmol) in water (0.3 mL) was heated to 205° C. for 0.5 h in a microwave oven then concentrated in vacuo. The residue was purified by chromatography (silica gel, 10 g, 200˜300 mesh, ethyl acetate:petroleum ether=1:30) to afford 6-(2,5-dimethylpyrrolidin-1-yl)pyridin-2-amine (0.383 g, 45%) as a yellow oil. LC-MS: [M+1]+=192, tR=1.048 min.

Workup

concentrationthen concentrated in vacuo
customThe residue was purified by chromatography (silica gel, 10 g, 200˜300 mesh, ethyl acetate:petroleum ether=1:30)

Sources & evidence

ORD record: ord-21a00443f3c24b4082e35363f2167375
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169259B2

Reaction notes

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