Sodium hydride → HCID 85916576, compound

HRID 1395230Notes

Reaction equation

HRID 1395230 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:9])[CH2:5][CH2:6][CH2:7][OH:8].Cl[C:11]1[C:16]2[CH:17]=[N:18][C:19]3[N:23]([CH2:24][CH3:25])[N:22]=[CH:21][C:20]=3[C:15]=2[N:14]2[N:26]=[CH:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:13]2[N:12]=1>C1C=CC=CC=1>[CH3:3][N:4]([CH3:9])[CH2:5][CH2:6][CH2:7][O:8][C:11]1[C:16]2[CH:17]=[N:18][C:19]3[N:23]([CH2:24][CH3:25])[N:22]=[CH:21][C:20]=3[C:15]=2[N:14]2[N:26]=[CH:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:13]2[N:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 766463-(Dimethylamino)-1-propanolHCID 85916602HCID 85916602, compound

Product 1

HCID 85916576HCID 85916576, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 3.6 g of sodium hydride in 100 ml of dry benzene 15.3 g of 3-(dimethylamino)propanol are added dropwise at reflux temperature with stirring. Heating is continued for 10 hours. After this time, 34.4 g of 5-chloro-8-ethyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester are added and the solution is refluxed for 5 additional hours. The solution is evaporated to dryness and the residue is treated with water, filtered off and recrystallized from ethyl acetate. 12 g of 5-[3-(dimethylamino)propoxy]-8-ethyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester are obtained (29.3%); m.p. 106°-107°.

Workup

  1. additionare added dropwise
  2. temperatureat reflux temperature
  3. temperatureHeating
  4. temperaturethe solution is refluxed for 5 additional hours
  5. customThe solution is evaporated to dryness
  6. additionthe residue is treated with water
  7. filtrationfiltered off
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6fa0cb2b99144b6da451b52471e8f620
Source dataset
uspto-grants-1980_05
Patent number
US04202899

Reaction notes

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