Ethylamine → 3-Ethylamino-6-methoxy-2-(methoxymethyloxy)methylpyridine

HRID 1710856Notes

Reaction equation

HRID 1710856 reaction equation
Br[C:2]1[C:3]([CH2:10][O:11][CH2:12][O:13][CH3:14])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.CC(C)([O-])C.[Na+].[CH2:21]([NH2:23])[CH3:22]>O1CCCC1>[CH2:21]([NH:23][C:2]1[C:3]([CH2:10][O:11][CH2:12][O:13][CH3:14])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1)[CH3:22]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 23676156Sodium t-butoxideHCID 672418193-Bromo-6-methoxy-2-[(methoxymethoxy)methyl]pyridine

Product 1

HCID 672423343-Ethylamino-6-methoxy-2-(methoxymethyloxy)methylpyridineYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromo-6-methoxy-2-[(methoxymethoxy)methyl]pyridine (1.50 g, 5.72 mmol), tris(dibenzylideneacetone)(chloroform)dipalladium(0) (592 mg, 0.572 mmol), (2-biphenyl)di-t-butylphosphine (680 mg, 2.28 mmol), sodium t-butoxide (1.65 g, 17.2 mmol) and ethylamine (2.0 M solution in tetrahydrofuran, 15 mL, 30 mmol) in tetrahydrofuran (15 mL) was warmed to 135° C. over 3 minutes under microwave irradiation (500 W). The reaction mixture was cooled, then filtered through Celite, and washed with ethyl acetate. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to obtain N-ethyl-6-methoxy-2-[(methoxymethoxy)methyl]pyridin-3-amine (954 mg, 74%) as yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through Celite
  3. washwashed with ethyl acetate
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-e1bd8317f3ef4e2f96c8ac2fd1954c82
Source dataset
uspto-grants-2010_09
Patent number
US07790737B2

Reaction notes

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