Potassium Carbonate → HCID 58550510, compound

HRID 1890993Notes

Reaction equation

HRID 1890993 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[CH:16][N:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[OH:24])[CH:13]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].Br[CH2:26][CH2:27][O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:26][CH2:27][O:28][CH3:29])[N:15]=[CH:16][N:17]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 136127571HCID 136127571, compound

Product 1

HCID 58550510HCID 58550510, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[6-(3-methanesulfonyl-phenylamino)-pyrimidin-4-yl]-phenol (reference example 49) (0.31 g, 0.94 mmol), 1-bromo-2-methoxy-ethane (0.516 g, 3.75 mmol), potassium carbonate (1.03 g, 7.5 mmol) and acetonitrile (15 mL) was refluxed for 8 h. Then the reaction mixture was evaporated, the residue was washed with water and purified by column chromatography on silica (eluent chloroform-ethanol 20:1) to give (3-methanesulfonyl-phenyl)-{6-[2-(2-methoxy-ethoxy)-phenyl}-pyrimidin-4-yl]-amine as colorless solid.

Workup

  1. temperaturewas refluxed for 8 h
  2. customThen the reaction mixture was evaporated
  3. washthe residue was washed with water
  4. custompurified by column chromatography on silica (eluent chloroform-ethanol 20:1)

Sources & evidence

ORD record
ord-3f0eca76e2f247248a01ccb88ee88f6b
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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