Acetonitrile → HCID 18985854, compound

HRID 2396679Notes

Reaction equation

HRID 2396679 reaction equation
O[C:2]1[C:3]2[N:13]=[CH:12][CH:11]=[CH:10][C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1.P(Cl)(Cl)([Cl:16])=O.C(#N)C>CN(C)C=O>[Cl:16][C:2]1[C:3]2[N:13]=[CH:12][CH:11]=[CH:10][C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 178503526HCID 178503526, compound

Product 1

HCID 18985854HCID 18985854, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 19.0 g (98 mmol) of 4-hydroxy-2-methylthiopyrido[3,2-d]pyrimidine, 36.5 mL (60 g, 390 mmol) of phosphorus oxychloride and 200 mL of acetonitrile was prepared and heated to reflux with stirring. Since not much appeared to happen, about 1 mL of N,N-dimethylformamide was added. The solids then all went into solution in about 10 min. After about 2 hours, the volatiles were removed by evaporation under reduced pressure and the residue was diluted with dichloromethane. The resulting mixture was carefully washed with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was diluted with hexane and the solids were recovered by filtration and dried to obtain 17.8 g of the title compound melting at 120°-121° C.

Workup

  1. customwas prepared
  2. temperatureheated
  3. temperatureto reflux
  4. waitAfter about 2 hours
  5. customthe volatiles were removed by evaporation under reduced pressure
  6. additionthe residue was diluted with dichloromethane
  7. washThe resulting mixture was carefully washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure
  10. additionThe residue was diluted with hexane
  11. filtrationthe solids were recovered by filtration
  12. customdried

Sources & evidence

ORD record
ord-f949a2b0821b404b84b9282748cae1d9
Source dataset
uspto-grants-1996_02
Patent number
US05494887

Reaction notes

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