Cesium carbonate → HCID 68728133, compound

HRID 2067907Notes

Reaction equation

HRID 2067907 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([F:16])=[C:13]([OH:15])[CH:14]=2)=[N:6][CH:7]=1.Br[CH2:18][CH2:19][OH:20].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([F:16])=[C:13]([CH:14]=2)[O:15][CH2:18][CH2:19][OH:20])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 58542237HCID 58542237, compound

Product 1

HCID 68728133HCID 68728133, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(5-bromopyrimidin-2-ylamino)-2-fluorophenol 45 (0.25 mmol), 2-bromoethanol (0.28 mmol) and cesium carbonate (0.36 mmol) in acetonitrile (3 mL) is heated to 100° C. for 12 h. The reaction is evaporated to dryness then re-dissolved in DCM. The organic mixture is washed with water and brine then dried over magnesium sulfate, filtered and reduced to dryness to yield 2-(5-(5-bromopyrimidin-2-ylamino)-2-fluorophenoxy)ethanol 46a as a brown solid which is used without further purification. MS (m/z) (M+1)+: 329.2.

Workup

  1. customThe reaction is evaporated to dryness
  2. dissolutionthen re-dissolved in DCM
  3. washThe organic mixture is washed with water and brine
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-fbad543322494afa9082cf82ac769cf2
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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