Bromine → 2-(4-Bromo-1H-pyrazol-1-yl)pyrimidine

HRID 1038121Notes

Reaction equation

HRID 1038121 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[Br:12]Br>C(O)(=O)C>[Br:12][C:4]1[CH:3]=[N:2][N:1]([C:6]2[N:7]=[CH:8][CH:9]=[CH:10][N:11]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 111707712-(1H-Pyrazol-1-yl)pyrimidine

Product 1

HCID 457897012-(4-Bromo-1H-pyrazol-1-yl)pyrimidineYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-pyrazol-1-yl-pyrimidine (0.55 g, 3.7 mmol) in acetic acid (5 mL) was added bromine (1.2 g, 7.5 mmol) in acetic acid (3 mL) dropwisely. After addition, the reaction mixture was stirred at room temperature overnight. After removed the acetic acid, the crude product was purified using column chromatography (2% methanol in dichloromethane) to give 0.7 g of pure product in 85% yield. MS (ESMS, M+H 225).

Workup

  1. additionAfter addition
  2. customAfter removed the acetic acid
  3. customthe crude product was purified

Sources & evidence

ORD record
ord-19f31f338b3a44819c22eb0230e11faa
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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