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 1395229Notes

Reaction equation

HRID 1395229 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-bf6f68a19460493cb5094834a29a5781
Source dataset
uspto-grants-1980_05
Patent number
US04202899

Reaction notes

Loading…