Dimethylformamide → 4-Chloro-2-(2-fluorophenyl)thieno[2,3-d]pyrimidine

HRID 1354293Notes

Reaction equation

HRID 1354293 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][S:14][C:12]=2[N:13]=1.S(Cl)([Cl:20])=O.CN(C)C=O>C(Cl)(Cl)Cl>[Cl:20][C:10]1[C:11]2[CH:16]=[CH:15][S:14][C:12]=2[N:13]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 211043032-(2-Fluoro-phenyl)-3H-thieno[2,3-d]pyrimidin-4-one

Product 1

HCID 211043364-Chloro-2-(2-fluorophenyl)thieno[2,3-d]pyrimidineYield 45.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(2-Fluoro-phenyl)-3H-thieno[2,3-d]pyrimidin-4-one (900 mg, 3.65 mmole) was dissolved in chloroform and thionyl chloride (0.532 ml, 7.30 mmole) was added to the mixture followed by 1 ml dimethylformamide. Heated the reaction mixture to reflux for 2.5 hours, the cooled mixture was washed with 10% sodium carbonate, dried the chloroform solution over sodium sulfate (anh) and removed solvent. The crude product was chromatographed on silica gel, eluting with chloroform. Upon removal of solvent obtained 438 mg product (yield: 45%).

Workup

  1. temperatureHeated the reaction mixture
  2. temperatureto reflux for 2.5 hours
  3. washthe cooled mixture was washed with 10% sodium carbonate
  4. dry with materialdried the chloroform solution over sodium sulfate (anh)
  5. customremoved solvent
  6. customThe crude product was chromatographed on silica gel
  7. washeluting with chloroform
  8. customUpon removal of solvent

Sources & evidence

ORD record
ord-05e905e18cfe408ca7e901b66950d7b5
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

Loading…