Ethanol → 6-Bromopyrazolo[1,5-a]pyrimidine

HRID 1255861Notes

Reaction equation

HRID 1255861 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[Br:7]/[C:8](=[CH:11]\N(C)C)/[CH:9]=O.C(O)C>C(O)(=O)C>[Br:7][C:8]1[CH:9]=[N:1][C:2]2[N:3]([N:4]=[CH:5][CH:6]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 215914792-Bromo-3-(dimethylamino)acroleinHCID 178418806HCID 178418806, compound

Product 1

HCID 222367016-Bromopyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Aminopyrazole (0.75 g, 9.04 mmol) was mixed with (2Z)-2-bromo-3-(dimethylamino)acrylaldehyde obtained at the previous step (1.85 g, 10.4 mmol). Absolute ethanol (20 mL) and glacial acetic acid (2 mL) were added. The reaction mixture was stirred under reflux for 16 h and evaporated to dryness. The residue was washed on a filter with cold ethanol/hexane mixture (3:1) and dried in a vacuum oven at 30° C. to give 6-bromopyrazolo[1,5-a]pyrimidine.

Workup

  1. customobtained at the previous step (1.85 g, 10.4 mmol)
  2. temperatureunder reflux for 16 h
  3. customevaporated to dryness
  4. washThe residue was washed on
  5. filtrationa filter with cold ethanol/hexane mixture (3:1)
  6. customdried in a vacuum oven at 30° C.

Sources & evidence

ORD record
ord-8193ef84867742bfaacde2bfec964037
Source dataset
uspto-grants-2013_06
Patent number
US08461162B2

Reaction notes

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