Water → 7-(methylthio)-2-(4-nitrophenyl)-2H-pyrazolo[4,3-d]pyrimidine

HRID 1926045Notes

Reaction equation

HRID 1926045 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[NH:11][N:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.CC(C)([O-])C.[K+].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.O>CN(C)C=O>[CH3:1][S:2][C:3]1[C:4]2[C:5](=[CH:9][N:10]([C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=3)[N:11]=2)[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 23665647Potassium tert-butoxideHCID 552958947-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine

Product 1

HCID 675207817-(methylthio)-2-(4-nitrophenyl)-2H-pyrazolo[4,3-d]pyrimidineYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (500 mg) in N,N-dimethylformamide (10 mL) was added potassium tert-butoxide (405 mg) under ice-cooling, and the mixture was stirred at room temperature for 10 min. Subsequently, 1-fluoro-4-nitrobenzene (465 mg) was added, and the mixture was stirred at 70° C. for 30 min. After the completion of the reaction, water was added to the reaction mixture and the mixture was stirred at room temperature for 30 min. The resultant solid was collected by filtration, washed with diisopropyl ether and dried to give the title compound (860 mg) as brown crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 70° C. for 30 min
  3. additionwas added to the reaction mixture
  4. stirringthe mixture was stirred at room temperature for 30 min
  5. filtrationThe resultant solid was collected by filtration
  6. washwashed with diisopropyl ether
  7. customdried

Sources & evidence

ORD record
ord-beb10a3bff684ed0b5a2945f0c1132b7
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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