Water → HCID 58169276, compound

HRID 1484980Notes

Reaction equation

HRID 1484980 reaction equation
[Br:1][C:2]1[N:7]=[C:6](Br)[C:5]([Cl:9])=[CH:4][N:3]=1.[C:10]([C:14]1[NH:18][N:17]=[C:16]([NH2:19])[CH:15]=1)([CH3:13])([CH3:12])[CH3:11].O.CC(=O)OCC>CCO>[Br:1][C:2]1[N:7]=[C:6]([NH:19][C:16]2[CH:15]=[C:14]([C:10]([CH3:13])([CH3:12])[CH3:11])[NH:18][N:17]=2)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 5227873-Amino-5-tert-butylpyrazoleHCID 58169229Pyrimidine, 2,4-dibromo-5-chloro-

Product 1

HCID 58169276HCID 58169276, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4-dibromo-5-chloropyrimidine (500 mg, 1.85 mmol) and 5-tert-butyl-1H-pyrazol-3-amine (216 mg, 2.2 mmol, 1.2 eq) in EtOH (100 mL) was stirred at rt for 2 h. After addition of water and extraction with EA (3×), the combined organic layers were dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography (EA/PE 1:2) to afford 2-bromo-N-(5-tert-butyl-1H-pyrazol-3-yl)-5-chloropyrimidin-4-amine (450 mg, 85%). LC-MS (m/z)=288 [M+H]+

Workup

  1. dry with materialthe combined organic layers were dried (Na2SO4)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (EA/PE 1:2)

Sources & evidence

ORD record
ord-d96fd5c041a2499aa06f47261cd406d5
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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