Pyrazole → 5-Bromo-2-(1H-pyrazol-1-yl)pyrimidine

HRID 2171262Notes

Reaction equation

HRID 2171262 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(N(C)C)=O.[Br:18][C:19]1[CH:20]=[N:21][C:22](Cl)=[N:23][CH:24]=1>O>[Br:18][C:19]1[CH:20]=[N:21][C:22]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[N:23][CH:24]=1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 457897835-Bromo-2-(1H-pyrazol-1-yl)pyrimidineYield 126.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Pyrazole (130 mg) and cesium carbonate (610 mg) were added to a DMAc (10 ml) solution containing 5-bromo-2-chloropyrimidine (300 mg), followed by stirring at 120° C. for 0.5 hours. The reaction mixture was adjusted to room temperature and water was added to the mixture. Next, the organic layers were collected, washed with saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and a yellow solid of 5-bromo-2-(pyrazol-1-yl)pyrimidine (440 mg) was thus obtained.

Workup

  1. customwas adjusted to room temperature
  2. customNext, the organic layers were collected
  3. washwashed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-b3b8573fc6f8424fb51a58e7edfbc329
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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