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

HRID 1786960Notes

Reaction equation

HRID 1786960 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

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 13387N-methyl-2-pyrrolidoneSolvent

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-0b4baa0c51a64f5cbaae72595b2c1da1
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

Loading…