Ethanol → HCID 178471745, compound

HRID 1906761Notes

Reaction equation

HRID 1906761 reaction equation
[C:1]1([N:7]2[C:16]([OH:17])=[C:10]3[N:11]=[CH:12][N:13]=[C:14]([SH:15])[C:9]3=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.C(=O)([O-])[O-].[K+].[K+].Br[C:28]([CH3:35])([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]>O>[C:1]1([N:7]2[C:16]([OH:17])=[C:10]3[N:11]=[CH:12][N:13]=[C:14]([S:15][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH3:35])[CH3:34])[C:9]3=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 178515258HCID 178515258, compound

Product 1

HCID 178471745HCID 178471745, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3.66 g of 2-phenyl-3-hydroxy-7-mercapto-pyrazolo [4,3-d]pyrimidine was suspended in a solvent mixture comprising 150 ml of ethanol and 30 ml of water, and 2.5 g of anhydrous potassium carbonate was added thereto. While heating the mixture to 80° C., 3.5 g of ethyl α-bromoisobutyrate was dropwise added thereto, and the heating was continued for further 6 hours. Then, the solvent was distilled off. Water was added to the residue and the residue was dissolved. The solution was acidified with hydrochloric acid, and then extracted with chloroform. The starting material insoluble in both the aqueous layer and the chloroform layer was collected by filtration and recovered (recovered amount: 1.5 g). The chloroform layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The remaining solid was recrystallized from acetone.

Workup

  1. additionwas added
  2. distillationThen, the solvent was distilled off
  3. additionWater was added to the residue
  4. dissolutionthe residue was dissolved
  5. extractionextracted with chloroform
  6. filtrationThe starting material insoluble in both the aqueous layer and the chloroform layer was collected by filtration
  7. customrecovered
  8. custom(recovered amount: 1.5 g)
  9. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off
  11. customThe remaining solid was recrystallized from acetone

Sources & evidence

ORD record
ord-8014343a4a3e437f820c4d979eb8b506
Source dataset
uspto-grants-1987_03
Patent number
US04654348

Reaction notes

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