2,2-Dimethylpyrrolidine → HCID 80653179, compound

HRID 1755342Notes

Reaction equation

HRID 1755342 reaction equation
F[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]1([CH3:15])[CH2:14][CH2:13][CH2:12][NH:11]1>O>[CH3:9][C:10]1([CH3:15])[CH2:14][CH2:13][CH2:12][N:11]1[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4147732,2-DimethylpyrrolidineHCID 27613996-Fluoropyridin-2-amine

Product 1

HCID 80653179HCID 80653179, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
205 °C

Procedure

A mixture of 6-fluoropyridin-2-amine (0.5 g, 4.46 mmol) and 2,2-dimethylpyrrolidine (0.67 g, 6.75 mmol) in water (0.3 mL) was heated to 205° C. for 0.5 h in a sealed tube 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=1:15) to afford 6-(2,2-dimethylpyrrolidin-1-yl)pyridin-2-amine (0.035 g, 4%) as a yellow oil. LC-MS: [M+1]+=192, tR=1.048 min.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by chromatography (silica gel, 10 g, 200˜300 mesh, ethyl acetate:petroleum ether=1:15)

Sources & evidence

ORD record
ord-b291b9b22e10400ca89fbd336b18c5b4
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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