Thionyl Chloride → 4-Chlorothieno[2,3-d]pyrimidine

HRID 1432159Notes

Reaction equation

HRID 1432159 reaction equation
[N:1]1[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[C:4](O)=[N:3][CH:2]=1.S(Cl)([Cl:13])=O>CN(C=O)C>[Cl:13][C:4]1[C:5]2[CH:9]=[CH:8][S:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178518067HCID 178518067, compound

Product 1

HCID 7366184-Chlorothieno[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of thieno[2,3-d]pyrimidin-4-ol derivative 3 (3.7 mmol), thionyl chloride (5.5 mL) and dry DMF (0.5 mL) was heated at reflux for 4 h. The reaction mixture was cooled to room temperature and the excess thionyl chloride was removed by vacuum distillation. To the resulting residue 200 g of ice was added and extracted with dichloromethane (3×100 mL). The combined organic layers were dried (Na2SO4) and concentrated. The product was purified by silica chromatography (100% DCM) to afford 4-Chloro-thieno[2,3-d]-pyrimidine 4 in 80-95% yields.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. customthe excess thionyl chloride was removed by vacuum distillation
  4. additionTo the resulting residue 200 g of ice was added
  5. extractionextracted with dichloromethane (3×100 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe product was purified by silica chromatography (100% DCM)

Sources & evidence

ORD record
ord-84a5c35192004f03aa65e2f9ddc5661d
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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