Water → 5-Methyl-3-(3-phenoxyazetidin-1-yl)pyrazin-2-amine

HRID 1622853Notes

Reaction equation

HRID 1622853 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]([CH:14]1[CH2:17][NH:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[C:19]1[C:20]([NH2:26])=[N:21][CH:22]=[C:23]([CH3:25])[N:24]=1.O>CN(C=O)C.CCOC(C)=O>[CH3:25][C:23]1[N:24]=[C:19]([N:16]2[CH2:17][CH:14]([O:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:15]2)[C:20]([NH2:26])=[N:21][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 98990432-Amino-3-bromo-5-methylpyrazineHCID 128125013-Phenoxyazetidine

Product 1

HCID 682809345-Methyl-3-(3-phenoxyazetidin-1-yl)pyrazin-2-amineYield 35.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Potassium carbonate (18.53 mg) was added to a mixture of 3-phenoxyazetidine (20 mg) and 3-bromo-5-methylpyrazin-2-amine (25 mg) in DMF (dry) (1 mL). The mixture was stirred at 120° C. for 4 hr. Water and EtOAc were added and the extracted organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (12 mg) as white solid.

Workup

  1. washthe extracted organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-5ef0ff8e82544d6eae7758785cb7c391
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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