Water → (4-Chloro-phenyl)-[6-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl]-amine

HRID 1961703Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.Cl[C:12]1[CH:17]=[N:16][CH:15]=[C:14]([N:18]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[N:19]2)[N:13]=1.O>CS(C)=O>[Cl:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:12]2[CH:17]=[N:16][CH:15]=[C:14]([N:18]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[N:19]3)[N:13]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 130 °C

Procedure

Sodium hydride (60% in mineral oil, 161 mg, 4.03 mmol) was added to a suspension of 4-chloroaniline (489 mg, 3.83 mmol) in dimethylsulfoxide (10 mL). The mixture was stirred at 130° C. for 5 minutes. 2-Chloro-6-(3,5-dimethyl-pyrazol-1-yl)-pyrazine was added and the resulting mixture was stirred at 130° C. for 30 minutes. Cooling, followed by addition of water gave a brown precipitate. The brown solid was collected by filtration, re-dissolved in ethyl acetate, washed with brine, dried over sodium sulphate, filtrated and evaporated. The crude product was purified by flash chromatography to give (4-chloro-phenyl)-[6-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl]-amine (318 mg, 55%) as a brown solid.

Workup

stirringthe resulting mixture was stirred at 130° C. for 30 minutes
temperatureCooling
customgave a brown precipitate
filtrationThe brown solid was collected by filtration
dissolutionre-dissolved in ethyl acetate
washwashed with brine
dry with materialdried over sodium sulphate
filtrationfiltrated
customevaporated
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-26dedc2f1c8f4517b1e5d221ffa44d2f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415358B2

Reaction notes

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