Potassium Carbonate → 6,7-Dihydro-7-ethoxycarbonyl-1-methylpyrazolo[3,4-d]thiazolo[3,2-a]pyrimidin-4(1H)-one

HRID 260520

Reaction equation

HRID 260520 reaction equation
[SH:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[CH:10]=[N:9][N:8]([CH3:11])[C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:20]([CH2:26]Br)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C)C=O>[CH2:24]([O:23][C:21]([CH:20]1[S:1][C:2]2=[N:7][C:6]3[N:8]([CH3:11])[N:9]=[CH:10][C:5]=3[C:4](=[O:12])[N:3]2[CH2:26]1)=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 97945Ethyl 2,3-dibromopropionateHCID 178481768HCID 178481768, compound

Product 1

HCID 224016666,7-Dihydro-7-ethoxycarbonyl-1-methylpyrazolo[3,4-d]thiazolo[3,2-a]pyrimidin-4(1H)-oneYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In 150 ml of dimethylformamide was dissolved 8.42 g (46.2 mmol) of 4,5-dihydro-6-mercapto-1-methylpyrazolo[3,4-d]pyrimidin-4(1H)-one [Helv. Chim. Acta, 42, 349 (1959)], and 12.8 g (92.4 mmol) of potassium carbonate and 18.0 ml (69.3 mmol) of ethyl 2,3-dibromopropionate were added to the solution, followed by stirring at 80° C. for 6 hours. After evaporation of the solvent, the residue was subjected to partition between chloroform and water, and the chloroform layer was concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform to give 3.16 g (24%) of Compound 42. The compound was recrystallized from ethanol for purification.

Workup

  1. additionwere added to the solution
  2. customAfter evaporation of the solvent
  3. customto partition between chloroform and water
  4. concentrationthe chloroform layer was concentrated to dryness under reduced pressure
  5. washeluted with chloroform

Sources & evidence

ORD record
ord-7bd0b4b92bd845bda711ce4ae95a4e60
Source dataset
uspto-grants-1996_06
Patent number
US05527908

Linked notes

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