Ethanol → 6-Hydroxy-7-oxo-3-phenyl-1,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl ester

HRID 1097744Notes

Reaction equation

HRID 1097744 reaction equation
[C:1]1([C:7]2[C:8]([NH2:12])=[N:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O/[C:17](/[C:26]([O-:28])=[O:27])=[C:18](/[O:22]C(=O)C)\[C:19]([O-:21])=O)(=O)C.[C:29]1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C>C(O)(C)C>[CH3:29][O:28][C:26]([C:17]1[N:12]=[C:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:11][NH:10][N:9]2[C:19](=[O:21])[C:18]=1[OH:22])=[O:27]

Participants

6

Reactant 4

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 86643055DiacetoxyfumarateHCID 178509246HCID 178509246, compound

Product 1

HCID 581011306-Hydroxy-7-oxo-3-phenyl-1,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl esterYield 567.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Phenyl pyrazole amine (100 mg, 0.63 mmol), diacetoxyfumarate (180 mg, 0.69 mmol) and p-toluenesulphonic acid (5 mg) were heated at 100° C. for 20 minutes before being cooled to room temperature and sonicated with ethanol: i-propanol for 10 min. The resulting precipitate was collected and washed with ethanol. The product was isolated as a yellow solid (47 mg, 26%).

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with ethanol

Sources & evidence

ORD record
ord-7b6a7d6559b9402cbc20e7f2cb0facc5
Source dataset
uspto-grants-2012_03
Patent number
US08143268B2

Reaction notes

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