Sodium Methoxide → 3-Pyridinamine, 4-chloro-2-methoxy-

HRID 1260456Notes

Reaction equation

HRID 1260456 reaction equation
Br[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][O-:11].[Na+]>CO>[Cl:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([O:11][CH3:10])[C:7]=1[NH2:8]

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 224762862-Bromo-4-chloropyridin-3-amine

Product 1

HCID 451221783-Pyridinamine, 4-chloro-2-methoxy-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-bromo-4-chloropyridin-3-amine (prepared as described in US2002/0119982) (1.0 eq.) in dry MeOH (0.25M) under argon was added a solution of NaOMe (25% wt in MeOH, 1.5 eq.) and the reaction mixture was refluxed for 1 h, more NaOMe (25% wt in MeOH, 1.5 eq) was added and the reaction mixture was refluxed for an additional 2 h. The volatiles were removed under reduced pressure and the crude product was purified by flash chromatography eluting with 2-10% EtOAc/petroleum ether affording the titled compound as yellow oil. 1H-NMR (300 MHz, DMSO-d6, 300K) δ 7.33 (1H, d, J=5.5 Hz), 6.88 (1H, d, J=5.5 Hz), 5.13 (2H, bs), 3.89 (3H, s). MS (ES) C6H7ClN2O requires: 158, found: 159, 161 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed for 1 h
  2. temperaturethe reaction mixture was refluxed for an additional 2 h
  3. customThe volatiles were removed under reduced pressure
  4. customthe crude product was purified by flash chromatography
  5. washeluting with 2-10% EtOAc/petroleum ether affording the titled compound as yellow oil

Sources & evidence

ORD record
ord-4752c620a0ce476781a4744e822ba63a
Source dataset
uspto-grants-2013_06
Patent number
US08470823B2

Reaction notes

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