Sodium hydride → HCID 86621091, compound

HRID 1988031Notes

Reaction equation

HRID 1988031 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[F:9][C:10]([F:25])([F:24])[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[CH:23]=[CH:22][CH:21]=[N:20]1)[OH:12].[H-].[Na+]>C1COCC1>[Cl:8][C:6]1[CH:7]=[C:2]([O:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:19]2[CH:23]=[CH:22][CH:21]=[N:20]2)[C:10]([F:9])([F:25])[F:24])[N:3]=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 66743460HCID 66743460, compound

Product 1

HCID 86621091HCID 86621091, compoundYield 112.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
42.5 °C

Procedure

4,6-Dichloro pyrimidine (0.082 g, 0.55 mmol), 2,2,2-trifluoro-1-(2-pyrazol-1-yl-phenyl)-ethanol (0.121 g, 0.50 mmol), NaH (0.03 g, 0.78 mmol) were added to anhydrous THF (10 ml) under nitrogen atmosphere. The reaction was stirred at 40-45° C. for 6 h, and then was cooled to room temperature, and quenched with water (0.2 ml). The reaction mixture was concentrated to give crude 4-chloro-6-[2,2,2-trifluoro-1-(2-pyrazol-1-yl-phenyl)-ethoxy]-pyrimidine (0.20 g, >90% pure by LCMS), which was directly used in the following step.

Workup

  1. temperaturewas cooled to room temperature
  2. customquenched with water (0.2 ml)
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-2cff6c13d260446bb57879e3952e338e
Source dataset
uspto-grants-2009_06
Patent number
US07553840B2

Reaction notes

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