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Methanol → 2-[(6-Methoxypyrazin-2-ylamino)methyl]phenol

HRID 2170003
Notes
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Reaction equation

HRID 2170003 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH:5]=[N:4][CH:3]=1.[CH3:17][OH:18].[OH-].[Na+].[Cl-].[NH4+]>C(OCC)(=O)C>[CH3:17][O:18][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH:5]=[N:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 53250722HCID 53250722, compound

Product 1

HCID 532507282-[(6-Methoxypyrazin-2-ylamino)methyl]phenol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

Introduced into a microwave tube are 363 mg (1.29 mmol) of 2-[(6-bromopyrazin-2-ylamino)methyl]phenol, prepared as described previously in Example 12, to which 3 ml of methanol and 103 mg (2.58 mmol, 2 eq) of sodium hydroxide are added. The reaction mixture is then heated for 30 mins in a microwave oven at 150° C. and is then diluted with 50 ml of ethyl acetate. The mixture is neutralized with an ammonium chloride solution to pH=7, decanted and the organic phase is washed twice with 50 ml of water. The organic phase is dried over magnesium sulphate, filtered, and concentrated to dryness. The residue is purified by chromatography over silica with, as eluent, heptane/ethyl acetate (7/3). 2-[(6-Methoxypyrazin-2-ylamino)methyl]phenol is obtained in the form of a white solid.

Workup

  1. additionIntroduced into a microwave tube
  2. customprepared
  3. additionare added
  4. customdecanted
  5. washthe organic phase is washed twice with 50 ml of water
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue is purified by chromatography over silica with, as eluent

Sources & evidence

ORD record
ord-23203c035d7f4028b25166ce670367ae
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09050266B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes