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Potassium Carbonate → 4-[N-(5,6-di-p-tolylpyrazin-2-yl)-N-methylamino]-1-butanol

HRID 1271275
Notes
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Reaction equation

HRID 1271275 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[N:3]=1.[CH3:22][NH:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:11]1([CH3:14])[CH:12]=[CH:13][C:8]([C:5]2[N:6]=[CH:7][C:2]([N:23]([CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[CH3:22])=[N:3][C:4]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98339374-(Methylamino)butan-1-olHCID 233239745-Chloro-2,3-bis(4-methylphenyl)pyrazine

Product 1

HCID 184526564-[N-(5,6-di-p-tolylpyrazin-2-yl)-N-methylamino]-1-butanolYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3.00 g of 2-chloro-5,6-di-p-tolylpyrazine and 1.57 g of 4-(methylamino)-1-butanol in 15 ml of N,N-dimethylformamide, 2.26 g of potassium carbonate was added. After heating with stirring at 100° C. for 26 hours, the reaction solution was extracted with diethyl ether after adding ice water. The extract was washed in turn with water and saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and the resulting crystal was washed with diisopropyl ether to obtain 2.76 g of the desired compound as a colorless crystal having a melting point of 94 to 96° C.

Workup

  1. temperatureAfter heating
  2. extractionthe reaction solution was extracted with diethyl ether
  3. additionafter adding ice water
  4. washThe extract was washed in turn with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. washthe resulting crystal was washed with diisopropyl ether

Sources & evidence

ORD record
ord-7cd95efa6d314b7182fd36d4a0008ee7
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07205302B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes