HCID 178418361, compound → HCID 178515172, compound

HRID 616566Notes

Reaction equation

HRID 616566 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:8](=[O:12])[N:7]3[N:13]=[CH:14][CH:15]=[C:6]3[NH:5][C:4]=2[CH:3]=1.[H][H]>C(N(CC)CC)C.[Pd].CN(C)C=O>[N:13]1[N:7]2[C:8](=[O:12])[C:9]3[CH:10]=[N:11][CH:2]=[CH:3][C:4]=3[NH:5][C:6]2=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178515173HCID 178515173, compound

Product 1

HCID 178515172HCID 178515172, compound

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

22 g. of 6-chloropyrazolo[1,5-a]pyrido[4,3-d]pyrimidin-9(4H)-one of Example 1 are hydrogenated in 200 ml. of dimethylformamide in the presence of 15 g. of triethylamine and 10% palladium on charcoal as catalyst at 80° and 3 atmospheres hydrogen pressure. When the theoretical amount of hydrogen has been absorbed, the reaction is stopped and the mixture is filtered after cooling to room temperature. After evaporation of the solvent, the crystalline residue, pyrazolo[1,5-a]pyrido[4,3-d]pyrimidin-9(4H)-one, is recrystallized from dimethylformamide, yield: 13 g. (70%); m.p. >300°.

Workup

  1. customat 80°
  2. customWhen the theoretical amount of hydrogen has been absorbed
  3. filtrationthe mixture is filtered
  4. customAfter evaporation of the solvent
  5. customthe crystalline residue, pyrazolo[1,5-a]pyrido[4,3-d]pyrimidin-9(4H)-one, is recrystallized from dimethylformamide, yield: 13 g

Sources & evidence

ORD record
ord-cde2fdf2632e4663af86616d5985c726
Source dataset
uspto-grants-1978_02
Patent number
US04075210

Reaction notes

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