m-Chloroperbenzoic acid → HCID 67424667, compound

HRID 1891044Notes

Reaction equation

HRID 1891044 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:12][NH:13][C:14]1[C:19]([C:20]#[N:21])=[CH:18][N:17]=[C:16](SC)[N:15]=1.[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1.O1CCCC1>[CH3:12][NH:13][C:14]1[C:19]([C:20]#[N:21])=[CH:18][N:17]=[C:16]([NH:35][C:34]2[CH:33]=[CH:32][C:31]([N:28]3[CH2:27][CH2:26][N:25]([CH3:24])[CH2:30][CH2:29]3)=[CH:37][CH:36]=2)[N:15]=1

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 106789344-(Methylamino)-2-(methylthio)pyrimidine-5-carbonitrile

Product 1

HCID 67424667HCID 67424667, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

248 mg of mCPBA was added to a 3:1 toluene-tetrahydrofuran (30 mL) solution containing 130 mg of 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carbonitrile, and the mixture was stirred at room temperature for 15 minutes. Then, 138 mg of 4-(4-methylpiperazin-1-yl)aniline, and 280 mg of DIPEA were added to the mixture, which was then stirred at 80° C. for 8 hours. The solvent was distilled away after cooling the reaction mixture. Then, water was added, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated saline, and the solution was concentrated after drying with anhydrous magnesium sulfate. The resulting crude product was purified by basic silica gel column chromatography, and 170 mg of a white solid was obtained as a subject compound.

Workup

  1. stirringwas then stirred at 80° C. for 8 hours
  2. distillationThe solvent was distilled away
  3. temperatureafter cooling the reaction mixture
  4. additionThen, water was added
  5. extractionthe solution was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated saline
  7. concentrationthe solution was concentrated
  8. dry with materialafter drying with anhydrous magnesium sulfate
  9. customThe resulting crude product was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-1600681f245e490bb5919a589cf73e65
Source dataset
uspto-grants-2013_08
Patent number
US08507505B2

Reaction notes

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