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

HRID 1271275Notes

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

Participants

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

temperatureAfter heating
extractionthe reaction solution was extracted with diethyl ether
additionafter adding ice water
washThe extract was washed in turn with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography
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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