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Cesium carbonate → HCID 86621082, compound

HRID 2426379
Notes
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Reaction equation

HRID 2426379 reaction equation
[F:1][C:2]([F:18])([F:17])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)[OH:4].[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C(OCC)(=O)C>[Cl:19][C:20]1[CH:25]=[C:24]([O:4][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:2]([F:1])([F:17])[F:18])[N:23]=[CH:22][N:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 709434,6-DichloropyrimidineHCID 66743562HCID 66743562, compound

Product 1

HCID 86621082HCID 86621082, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
110 °C

Procedure

The mixture of 2,2,2-trifluoro-1-(2-pyridin-4-yl-phenyl)ethanol (100 mg, 0.40 mmol), 4,6-dichloro-pyrimidine (54 mg, 0.38 mmol), cesium carbonate (468 mg, 1.44 mmol) and 1,4-dioxane (1 ml). The mixture was heated at 110° C. overnight. The reaction mixture was cooled to room temperature. 10 ml of ethyl acetate was added, and then the mixture was filtered through Celite. The filtrate was concentrated to give 110 mg of 4-chloro-6-[2,2,2-trifluoro-1-(2-pyridin-4-yl-phenyl)-ethoxy]-pyrimidine, yield: 76%.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-82db83ba9137422dbb110c838f5d931d
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968559B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes