2-Bromopropanedial → 6-Bromo-3-pyridin-2-yl-pyrazolo[1,5-a]pyrimidin-2-ylamine

HRID 490111Notes

Reaction equation

HRID 490111 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([NH2:13])=[N:9][NH:10][C:11]=1[NH2:12].[Br:14][CH:15]([CH:18]=O)[CH:16]=O>C(O)C.C(O)(=O)C>[Br:14][C:15]1[CH:16]=[N:12][C:11]2[N:10]([N:9]=[C:8]([NH2:13])[C:7]=2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:18]=1

Participants

5

Reactant 2

HCID 749452-BromopropanedialHCID 576745884-(Pyridin-2-yl)-1H-pyrazole-3,5-diamine

Product 1

HCID 116378516-Bromo-3-pyridin-2-yl-pyrazolo[1,5-a]pyrimidin-2-ylamineYield 19.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

4-(Pyridin-2-yl)-1H-pyrazole-3,5-diamine (2.54 g, 14.51 mmol) and 2-bromo-malonaldehyde (2.41 g, 15.97 mmol) were suspended in dry ethanol (35 mL). A small amount of glacial acetic acid (30 drops) was added and the mixture was heated at reflux for 3 hours. After allowing the reaction to cool to room temperature the mixture was concentrated under reduced pressure. The resulting solid was purified by silica gel chromatography eluting with EtOAc containing 2% NH3(aq) solution to afford the title compound as a yellow solid (0.82 g, 19% yield). MS (ES+) 290/292. δH (DMSO-d6) 7.2 (3H, m), 7.9 (1H, t), 8.5 (1H, d), 8.6 (2H, m), 9.3 (1H, s).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customthe reaction
  4. concentrationwas concentrated under reduced pressure
  5. customThe resulting solid was purified by silica gel chromatography
  6. washeluting with EtOAc containing 2% NH3(aq) solution

Sources & evidence

ORD record
ord-4867144d143b41099301c415aa7a9ccb
Source dataset
uspto-grants-2009_05
Patent number
US07528138B2

Reaction notes

Loading…