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1,4-Dibromobutane → 1-Methyl-6,7,8,9-tetrahydropyrazolo[3',4':4,5]pyrimido[2,1-b]-[1,3]thiazepin-4(1H)-one

HRID 260523
Notes
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Reaction equation

HRID 260523 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[CH2:20][CH2:21][CH2:22][CH2:23]Br>CN(C)C=O>[CH3:11][N:8]1[C:6]2[N:7]=[C:2]3[N:3]([C:4](=[O:12])[C:5]=2[CH:10]=[N:9]1)[CH2:23][CH2:22][CH2:21][CH2:20][S:1]3
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 178481768HCID 178481768, compound

Product 1

HCID 224017091-Methyl-6,7,8,9-tetrahydropyrazolo[3',4':4,5]pyrimido[2,1-b]-[1,3]thiazepin-4(1H)-oneYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In 120 ml of dimethylformamide was dissolved 6.0 g (32.9 mmol) of 4,5-dihydro-6-mercapto-1-methylpyrazolo[3,4-d]pyrimidin-4(1H)-one [Helv. Chim. Acta, 42, 349 (1959)], and 13.7 g (98.8 mmol) of potassium carbonate and 5.90 ml (49.4 mmol) of 1,4-dibromobutane 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 1.71 g (22%) of Compound 45. 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-14f49c318af843eaadb79bd83c555c11
Source dataset
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05527908

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes