Sodium hydride → HCID 86621091, compound

HRID 1620839Notes

Reaction equation

HRID 1620839 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 (0.03g, 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-5de3812271ee4f02899d87210517a1fb
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Reaction notes

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