Dimethylformamide → 2-Methylpyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-5(4H)-one

HRID 1833338Notes

Reaction equation

HRID 1833338 reaction equation
Cl[C:2]1[N:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[N:9]([N:10]=[C:11]([CH3:13])[CH:12]=3)[C:4]=2[CH:3]=1.CN(C)C=O.[H][H]>[Pd].C(N(CC)CC)C>[CH3:13][C:11]1[CH:12]=[C:8]2[NH:7][C:6](=[O:14])[C:5]3[CH:15]=[N:16][CH:2]=[CH:3][C:4]=3[N:9]2[N:10]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 1360252228-chloro-2-methylpyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-5(4H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 1361423592-Methylpyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-5(4H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

2.3 g. of 8-chloro-2-methylpyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-5(4H)-one are hydrogenated in 50 ml. of dimethylformamide in the presence of 10% palladium on charcoal and 2 g. of triethylamine at 80° and 3 atmospheres hydrogen pressure. When the hydrogen absorption ceases, the solution is heated to reflux temperature and then filtered. After addition of 20 ml. of water, 2-methylpyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-5(4H)-one crystallizes, yield: 1.8 g. (90%); m.p. > 300°.

Workup

  1. customat 80°
  2. customWhen the hydrogen absorption ceases
  3. temperaturethe solution is heated
  4. temperatureto reflux temperature
  5. filtrationfiltered
  6. additionAfter addition of 20 ml
  7. customof water, 2-methylpyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-5(4H)-one crystallizes

Sources & evidence

ORD record
ord-8dba68d2b5644fb4b5782b273f04bb00
Source dataset
uspto-grants-1978_01
Patent number
US04066645

Reaction notes

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