3-Chloro-3-(3-pyridinyl)-2-propenal → 2-Furanyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone

HRID 1247947Notes

Reaction equation

HRID 1247947 reaction equation
Cl[C:2]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[CH:3][CH:4]=O.[NH2:12][C:13]1[C:17]([C:18]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)=[O:19])=[CH:16][NH:15][N:14]=1>C(O)(=O)C>[O:21]1[CH:22]=[CH:23][CH:24]=[C:20]1[C:18]([C:17]1[CH:16]=[N:15][N:14]2[C:2]([C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)=[CH:3][CH:4]=[N:12][C:13]=12)=[O:19]

Participants

4

Reactant 2

HCID 538697343-Chloro-3-(3-pyridinyl)-2-propenalHCID 178509268HCID 178509268, compound

Product 1

HCID 134758992-Furanyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.02 mole of 3-chloro-3-(3-pyridinyl)-2-propenal and 0.02 mole of (3-amino-1H-pyrazol-4-yl)-2-furanyl-methanone in 30 ml of glacial acetic acid was refluxed for 5 hours. The solvent was removed in vacuo and the residue partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The dichloromethane layer was dried over sodium sulfate and passed through a short pad of hydrous magnesium silicate. The eluent was concentrated and the residue crystallized from dichloromethane:hexane to give the desired product as crystals, mp 228°-229° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between saturated aqueous sodium bicarbonate and dichloromethane
  4. dry with materialThe dichloromethane layer was dried over sodium sulfate
  5. concentrationThe eluent was concentrated
  6. customthe residue crystallized from dichloromethane

Sources & evidence

ORD record
ord-ab10334a5142416eb34194ec17d02478
Source dataset
uspto-grants-1985_06
Patent number
US04521422

Reaction notes

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