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Water → methyl 4-[7-(methylthio)-2H-pyrazolo[4,3-d]pyrimidin-2-yl]benzoate

HRID 1926047
Notes
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Reaction equation

HRID 1926047 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.F[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[CH3:1][S:2][C:3]1[C:4]2[C:5](=[CH:9][N:10]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=3)[N:11]=2)[N:6]=[CH:7][N:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoateHCID 552958947-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine

Product 1

HCID 67520899methyl 4-[7-(methylthio)-2H-pyrazolo[4,3-d]pyrimidin-2-yl]benzoateYield 49.8%

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
120 °C

Procedure

To a solution of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (100 mg) and methyl 4-fluorobenzoate (102 mg) in 1-methyl-2-pyrrolidone (2 mL) was added potassium carbonate (125 mg), and the mixture was stirred at 120° C. for 3 hrs. 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 (90 mg) as yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-59998ee041cc4fae99ae69b4ac05825a
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178543B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes