Hydrogen Bromide → (4-Fluorophenyl)(4-((5-methyl-1H-pyrazol-3-yl)amino)quinazolin-2-yl)methanol hydrobromide

HRID 472162Notes

Reaction equation

HRID 472162 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[OH:9])=[CH:4][CH:3]=1.[BrH:27]>C(O)C>[BrH:27].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[OH:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 46892373Ac-430

Product 1

HCID 56837828(4-Fluorophenyl)(4-((5-methyl-1H-pyrazol-3-yl)amino)quinazolin-2-yl)methanol hydrobromideYield 86,216.703%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
27.5 °C

Procedure

A mixture of (4-fluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanol (260 g, 0.744 mol) and ethanol (2.86 L) in a round bottom flask under nitrogen was heated at reflux for 30 to 40 min, and then 48% aq. HBr (125.5 g, 0.744 mmol) was added while maintaining reflux. The mixture was allowed to cool to 25-30° C., and the mixture was stirred at 25-30° C. for 1 hr. The solid was collected by filtration, washing thoroughly with fresh ethanol (0.52 L). The solid was dried at 55 to 65° C. for 12 to 14 hrs to afford (4-fluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanol hydrobromide (276 g, 86%). HPLC (AUC) 99.9%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 to 40 min
  3. temperaturewhile maintaining
  4. temperaturereflux
  5. filtrationThe solid was collected by filtration
  6. washwashing thoroughly with fresh ethanol (0.52 L)
  7. customThe solid was dried at 55 to 65° C. for 12 to 14 hrs

Sources & evidence

ORD record
ord-7c05007b15a04d76a3332166a621cd0e
Source dataset
uspto-grants-2014_01
Patent number
US08633209B2

Reaction notes

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