Water → 2-[4-bromo-5-(4-fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]pyrimidine

HRID 1029466Notes

Reaction equation

HRID 1029466 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[N:19]=[C:18]([CH:27]([CH3:29])[CH3:28])[CH:17]=2)=[CH:12][CH:11]=1.O>CN(C=O)C>[Br:1][C:17]1[C:18]([CH:27]([CH3:29])[CH3:28])=[N:19][N:20]([C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:16]=1[C:13]1[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 148513212-[5-(4-Fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]pyrimidine

Product 1

HCID 148513232-[4-bromo-5-(4-fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]pyrimidineYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Bromosuccinimide (9.97 g, 0.056 mol) was added to a solution of 2-[5-(4-fluorophenyl)-3-(l-methylethyl)-1H-pyrazol-1-yl]pyrimidine (15.8 g, 0.056 mol) in DMF at 0° C. The resulting mixture was allowed to warm to room temperature over 24 hours. This was then poured into 500 mL water. The white solid which precipitated was collected by filtration and dried to yield 16.7 g of 2-[4-bromo-5-(4-fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]pyrimidine (3), mp 130°-133° C.

Workup

  1. customThe white solid which precipitated
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-1cf6b2647cab4f7fbb85b89b9c8d439b
Source dataset
uspto-grants-1992_04
Patent number
US05102893

Reaction notes

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