HCID 178422346, compound → HCID 178422347, compound

HRID 616568Notes

Reaction equation

HRID 616568 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:8](=[O:12])[N:7]3[N:13]=[C:14]([CH3:16])[CH:15]=[C:6]3[NH:5][C:4]=2[CH:3]=1>C(N(CC)CC)C.[Pd].CN(C)C=O>[CH3:16][C:14]1[CH:15]=[C:6]2[NH:5][C:4]3[CH:3]=[CH:2][N:11]=[CH:10][C:9]=3[C:8](=[O:12])[N:7]2[N:13]=1

Participants

5

Reactant 1

HCID 178422346HCID 178422346, compound

Product 1

HCID 178422347HCID 178422347, compound

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

23.5 g. of 6-chloro-2-methylpyrazolo[1,5-a]pyrido[4,3-d]pyrimidin-9(4H)-one of Example 3 are hydrogenated at 80° in 200 ml. of dimethylformamide in the presence of 15 g. of triethylamine and 10% palladium on charcoal as catalyst. When the theoretical amount of hydrogen has been absorbed, the reaction mixture is filtered hot and the mother liquor evaporated in vacuo to dryness. The remaining 2-methylpyrazolo[1,5-a]pyrido[4,3-d]pyrimidin-9(4H)-one is recrystallized from dimethylformamide, yield: 18.5 g. (92%); m.p. >300°.

Workup

  1. customare hydrogenated at 80° in 200 ml
  2. customWhen the theoretical amount of hydrogen has been absorbed
  3. filtrationthe reaction mixture is filtered hot
  4. customthe mother liquor evaporated in vacuo to dryness
  5. customThe remaining 2-methylpyrazolo[1,5-a]pyrido[4,3-d]pyrimidin-9(4H)-one is recrystallized from dimethylformamide, yield: 18.5 g

Sources & evidence

ORD record
ord-54561e92eb9541ccbe54eeee8452b8f7
Source dataset
uspto-grants-1978_02
Patent number
US04075210

Reaction notes

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