Sodium hydride → 5-chloro-N-(2-(isopropylsulfonyl)phenyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 1896086Notes

Reaction equation

HRID 1896086 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.[CH:12]([S:15]([C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20])(=[O:17])=[O:16])([CH3:14])[CH3:13].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[S:15]([CH:12]([CH3:14])[CH3:13])(=[O:17])=[O:16])[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 110741545,7-Dichloropyrazolo[1,5-a]pyrimidineHCID 126463662-(Propane-2-sulfonyl)aniline

Product 1

HCID 583753895-chloro-N-(2-(isopropylsulfonyl)phenyl)pyrazolo[1,5-a]pyrimidin-7-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5,7-dichloro-pyrazolo[1,5-a]pyrimidine (1.0 mmol) and 2-(isopropylsulfonyl)aniline(1.0 mmol) in 5 mL of DMF, was added carefully NaH (24 mg). The resulting suspension was stirred at 50° C. for 2 hours. After cooling at RT and careful quenching (ice), water was added and the mixture was extracted with EtOAc. The organic layers were collected, dried (Na2SO4), filtrated and concentrated. The residue was purified over SiO2 column chromatography (eluent: 9:1 Hexane:EtOAc), to give the desired 5-chloro-N-(2-(isopropylsulfonyl)phenyl)pyrazolo[1,5-a]pyrimidin-7-amine. MS (ES+): 351.06 (M+1)+.

Workup

  1. temperatureAfter cooling at RT
  2. customcareful quenching (ice), water
  3. additionwas added
  4. extractionthe mixture was extracted with EtOAc
  5. customThe organic layers were collected
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltrated
  8. concentrationconcentrated
  9. customThe residue was purified over SiO2 column chromatography (eluent: 9:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-5fe06219ef4442ba80f0705b978998ec
Source dataset
uspto-grants-2013_08
Patent number
US08518931B2

Reaction notes

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