Dimethylamine → HCID 22674480, compound

HRID 1005712Notes

Reaction equation

HRID 1005712 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.[CH3:22][NH:23][CH3:24].O>CCO>[CH3:22][N:23]([CH3:24])[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

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 22674366HCID 22674366, compound

Product 1

HCID 22674480HCID 22674480, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-bromo-2-thienyl 2-trifluoromethylthieno[3,2-d]pyrimidin-4-ylmethanone (0.3 g, 0.76 mmol) in EtOH (20 mL) was treated with 40% aqueous dimethylamine (5 mL), refluxed for 1 h, cooled, treated with water (25 mL), concentrated in vacuo and the aqueous mixture extracted with EtOAc (2×25 mL), the combined extracts washed with brine (25 mL), dried (MgSO4) and concentrated in vacuo. The resulting red oil was purified by chromatography [SiO2; heptane-EtOAc (1:1)] to give the title compound (0.115 g, 42%) as a red solid.

Workup

  1. temperaturerefluxed for 1 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. extractionthe aqueous mixture extracted with EtOAc (2×25 mL)
  5. washthe combined extracts washed with brine (25 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting red oil was purified by chromatography [SiO2; heptane-EtOAc (1:1)]

Sources & evidence

ORD record
ord-25b5ca99e07b48ad86d35950c2284f37
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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