4'-Mercaptoacetanilide → N-(4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-phenylpyrimidin-2-ylthio)phenyl)acetamide

HRID 1013898Notes

Reaction equation

HRID 1013898 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:10][N:11]=[C:12]([CH3:14])[CH:13]=2)[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[C:21]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[CH:27][CH:26]=1)(=[O:23])[CH3:22]>C(O)(C)(C)C>[C:21]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([S:31][C:2]2[N:7]=[C:6]([NH:8][C:9]3[NH:10][N:11]=[C:12]([CH3:14])[CH:13]=3)[CH:5]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:3]=2)=[CH:27][CH:26]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 707774'-MercaptoacetanilideHCID 178418761(2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine

Product 1

HCID 178419061N-(4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-phenylpyrimidin-2-ylthio)phenyl)acetamideYield 85%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

The above prepared (2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine (60 mg, 0.21 mmol) is combined with 4-acetamidothiophenol (176 mg, 1.05 mmol) in tert-butanol (5 mL) and the mixture heated at reflux for 20 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and aqueous NaHCO3. The organic layer is washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue is purified by flash chromatography (SiO2, DCM/MeOH gradient) to afford [2-(4-acetamido-phenylsulfanyl)-6-phenyl-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (74 mg, 85%)

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 20 hours
  3. custompartitioned between ethyl acetate and aqueous NaHCO3
  4. washThe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is purified by flash chromatography (SiO2, DCM/MeOH gradient)

Sources & evidence

ORD record
ord-22f2c41db3ca4acfa23b8b027de31ba0
Source dataset
uspto-grants-2011_07
Patent number
US07982037B2

Reaction notes

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