(R)-2-Methylpyrrolidine → (R)-6-(2-methylpyrrolidin-1-yl)pyridin-2-amine

HRID 1755322Notes

Reaction equation

HRID 1755322 reaction equation
F[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][NH:11]1>O>[CH3:9][C@@H:10]1[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 641544(R)-2-MethylpyrrolidineHCID 27613996-Fluoropyridin-2-amine

Product 1

HCID 86682708(R)-6-(2-methylpyrrolidin-1-yl)pyridin-2-amineYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
205 °C

Procedure

A suspension of 6-fluoropyridin-2-amine (448 mg, 4 mmol) and (R)-2-methylpyrrolidine (511 mg, 6 mmol) in water (0.5 mL) was heated to 205° C. in a microwave oven for 30 minutes. The reaction mixture was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give (R)-6-(2-methylpyrrolidin-1-yl)pyridin-2-amine (581 mg, 82%) as a light yellow oil. LC-MS: [M+H]+, 178.2, tR=1.049 min.

Workup

  1. customThe reaction mixture was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-6c93e383f7eb41159282fc87a3668c74
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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