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

HRID 1010824Notes

Reaction equation

HRID 1010824 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%

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. The reaction mixture was heated to reflux for 2.5 hours, the cooled mixture was washed with 10% sodium carbonate, the chloroform solution was dried over sodium sulfate (anh) and the solvent was removed. The crude product was chromatographed on silica gel, eluting with chloroform. Upon removal of solvent 438 mg of product was obtained (yield: 45%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. washthe cooled mixture was washed with 10% sodium carbonate
  4. dry with materialthe chloroform solution was dried over sodium sulfate (anh)
  5. customthe solvent was removed
  6. customThe crude product was chromatographed on silica gel
  7. washeluting with chloroform
  8. customUpon removal of solvent 438 mg of product
  9. customwas obtained (yield: 45%)

Sources & evidence

ORD record
ord-5c4423513457455d9fc39ed57b8e2214
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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