Water → HCID 58958590, compound

HRID 915569Notes

Reaction equation

HRID 915569 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([CH3:11])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:12]Br.O.[OH-].[K+]>C(O)(=O)C>[Br:12][C:9]1[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6][N:7]([CH3:11])[C:8]=1[NH2:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24408BromineHCID 27352873-tert-Butyl-1-methyl-1H-pyrazol-5-amine

Product 1

HCID 58958590HCID 58958590, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3-tert-butyl-1-methyl-1H-pyrazol-5-amine (10 g, 65.3 mmol) in acetic acid (90 mL) was added bromine (10.4 g, 65.26 mmol) in acetic acid (10 mL). The solution was stirred at rt for 30 min, and then water (100 mL) was added. The reaction mixture was basified to pH 9 using KOH (1.0 M ice cold solution). The resulting brown solid was filtered, collected, and purified by silica gel flash chromatography using 10 to 30% ethyl acetate in hexanes to afford 13.2 g (87%) of the title compound (white solid).

Workup

  1. filtrationThe resulting brown solid was filtered
  2. customcollected
  3. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-7767cd95789d42e3b41dba14b2e531a4
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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