Sodium hydride → 5-[3-(Dimethylamino)propoxy]-8-ethyl-2-methyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine

HRID 224625Notes

Reaction equation

HRID 224625 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]=[C:27]([CH3:29])[CH:28]=[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]=[C:27]([CH3:29])[CH:28]=[C:13]2[N:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 766463-(Dimethylamino)-1-propanolHCID 537035595-chloro-8-ethyl-2-methyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine

Product 1

HCID 233316325-[3-(Dimethylamino)propoxy]-8-ethyl-2-methyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine

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 and the mixture is refluxed for 6 hours. After this time, 28.6 g of 5-chloro-8-ethyl-2-methyl-8H-pyrazolo[1,5-a]-pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine are added in small portions with stirring. The solution is refluxed for 10 hours, and then the solvent is distilled off. The residue is treated with water, filtered off and recrystallized from ethyl acetate, yield 25 g (71%); m.p. 62°-64°.

Workup

  1. additionare added
  2. temperaturethe mixture is refluxed for 6 hours
  3. temperatureThe solution is refluxed for 10 hours
  4. distillationthe solvent is distilled off
  5. additionThe residue is treated with water
  6. filtrationfiltered off
  7. customrecrystallized from ethyl acetate, yield 25 g (71%)

Sources & evidence

ORD record
ord-8d85d89c78bd41939562094cbdc00dc7
Source dataset
uspto-grants-1980_11
Patent number
US04233300

Reaction notes

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