Methanol → 2-[(6-Methoxypyrazin-2-ylamino)methyl]phenol
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- additionIntroduced into a microwave tube
- customprepared
- additionare added
- customdecanted
- washthe organic phase is washed twice with 50 ml of water
- dry with materialThe organic phase is dried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated to dryness
- customThe residue is purified by chromatography over silica with, as eluent
Sources & evidence
- ORD record
- ord-23203c035d7f4028b25166ce670367ae
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09050266B2
Reaction notes
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