Benzo(b)thiophen-4-ol → 4-(Benzo[b]thiophen-4-yloxy)-6-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 857679Notes

Reaction equation

HRID 857679 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]2[C:8]([OH:12])=[CH:9][CH:10]=[CH:11][C:4]1=2.Cl[C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[N:17]=[CH:16][N:15]=1>CN(C=O)C>[S:3]1[CH:7]=[CH:6][C:5]2[C:8]([O:12][C:14]3[CH:19]=[C:18]([C:20]4[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:25]=4)[N:17]=[CH:16][N:15]=3)=[CH:9][CH:10]=[CH:11][C:4]1=2

Participants

5

Reactant 3

HCID 19217Benzo(b)thiophen-4-olHCID 24758Sodium hydrideHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

Product 1

HCID 218651554-(Benzo[b]thiophen-4-yloxy)-6-(4-trifluoromethyl-phenyl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.104 g, 2.6 mmol, 60% suspension in mineral oil, Aldrich) was added in small portions to a solution of benzo[b]thiophen-4-ol (0.3 g, 2 mmol, prepared according WO 01/68653) in DMF (4 mL) and the mixture was stirred at room temperature for 0.5 h. (4-Chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (0.776 g, 3 mmol) was then added and the mixture was stirred at room temperature for 18 h. The solvent was evaporated under vacuum, the residue was dissolved in EtOAc (50 mL), washed with 1 N NaOH and water, dried over MgSO4, and filtered. The filtrate was evaporated under vacuum and the residue purified by silica gel chromatography (10% EtOAc in hexanes) to give the title compound. Mp: 122.3–122.4° C. MS (ESI, pos. ion) m/z: 373.1 (M+1).

Workup

  1. additionwas then added
  2. customThe solvent was evaporated under vacuum
  3. dissolutionthe residue was dissolved in EtOAc (50 mL)
  4. washwashed with 1 N NaOH and water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated under vacuum
  8. customthe residue purified by silica gel chromatography (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e13691db01384d35b45f30b8400344c4
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

Loading…