2-(Methoxymethyl)pyrrolidine → 6-(2-(Methoxymethyl)pyrrolidin-1-yl)pyridin-2-amine

HRID 1755346Notes

Reaction equation

F[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][NH:13]1>O>[CH3:9][O:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][N:13]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-(methoxymethyl)pyrrolidine (0.617 g, 5.35 mmol) in water (0.2 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-(methoxymethyl)pyrrolidin-1-yl)pyridin-2-amine (0.68 g, 74%) as a yellow oil. LC-MS: [M+1]+=208, tR=1.052 min.

Workup

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

Sources & evidence

ORD record: ord-3cfb858b036c4bd9ab55d2f5263d1538
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169259B2

Reaction notes

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