Water → HCID 22674461, compound

HRID 1005713Notes

Reaction equation

HRID 1005713 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([C:9]2[C:10]3[S:21][CH:20]=[CH:19][C:11]=3[N:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)=[O:8])=[CH:4][CH:3]=1.C[O-].[Na+].[O:25]1CCOC[CH2:26]1.O>CO>[CH3:26][O:25][C:2]1[S:6][C:5]([C:7]([C:9]2[C:10]3[S:21][CH:20]=[CH:19][C:11]=3[N:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 10942334Sodium MethoxideHCID 22674366HCID 22674366, compound

Product 1

HCID 22674461HCID 22674461, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 5-bromo-2-thienyl 2-trifluoromethylthieno[3,2-d]pyrimidin-4-ylmethanone (0.2 g, 0.51 mmol) in MeOH (15 mL) was treated with sodium methoxide (0.11 g, 2.04 mmol), refluxed for 1 h, treated with dioxane (0.1 mL) to aid dissolution, refluxed for 18 h, cooled, treated with water (15 mL) and concentrated in vacuo. The resulting aqueous mixture was extracted with EtOAc (2×25 mL), the combined extracts washed with brine (25 mL), dried (MgSO4), concentrated in vacuo and the resulting red oil dissolved in heptane-EtOAc (50:50), filtered through a pad of SiO2, concentrated in vacuo and the resulting solid recrystallised [heptane-EtOAc (19:1)] to give the title compound (0.124 g, 71%) as a yellow solid.

Workup

  1. temperaturerefluxed for 1 h
  2. dissolutiondissolution
  3. temperaturerefluxed for 18 h
  4. temperaturecooled
  5. concentrationconcentrated in vacuo
  6. extractionThe resulting aqueous mixture was extracted with EtOAc (2×25 mL)
  7. washthe combined extracts washed with brine (25 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. dissolutionthe resulting red oil dissolved in heptane-EtOAc (50:50)
  11. filtrationfiltered through a pad of SiO2
  12. concentrationconcentrated in vacuo
  13. customthe resulting solid recrystallised [heptane-EtOAc (19:1)]

Sources & evidence

ORD record
ord-52ec405081a44d798f54aa3701e9f48d
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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