Thionyl Chloride → HCID 15295214, compound

HRID 725831Notes

Reaction equation

HRID 725831 reaction equation
O[C:2]1[C:3]2[N:11]=[C:10]([NH:12][CH:13]3[CH2:15][CH2:14]3)[N:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.S(Cl)([Cl:18])=O>CN(C)C=O>[Cl:18][C:2]1[C:3]2[N:11]=[C:10]([NH:12][CH:13]3[CH2:15][CH2:14]3)[N:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178518034HCID 178518034, compound

Product 1

HCID 15295214HCID 15295214, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

1.7 g of 4-hydroxy-6-(cyclopropylamino)-pyrimido[5,4-d]pyrimidine are heated under reflux with 50 ml of thionyl chloride with the addition of 4 drops of dimethylformamide for 1.5 hours. The reaction mixture is concentrated, methylene chloride is added and the mixture is concentrated again. The residue is then partitioned between methylene chloride and an aqueous potassium carbonate solution. The aqueous phase is extracted twice more with methylene chloride and the combined organic phases are dried and concentrated. The product is reacted further without further purification.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionmethylene chloride is added
  3. concentrationthe mixture is concentrated again
  4. customThe residue is then partitioned between methylene chloride
  5. extractionThe aqueous phase is extracted twice more with methylene chloride
  6. customthe combined organic phases are dried
  7. concentrationconcentrated
  8. customThe product is reacted further without further purification

Sources & evidence

ORD record
ord-2ceff2785ec1417fb2fcef57a2c1c6d2
Source dataset
uspto-grants-1998_01
Patent number
US05707989

Reaction notes

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