Phosphorus oxychloride → 5-chloro-8-ethyl-2-methyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine

HRID 224617Notes

Reaction equation

HRID 224617 reaction equation
[CH2:1]([N:3]1[C:7]2[N:8]=[CH:9][C:10]3[C:11](=O)[NH:12][C:13]4[N:14]([N:16]=[C:17]([CH3:19])[CH:18]=4)[C:15]=3[C:6]=2[CH:5]=[N:4]1)[CH3:2].P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:11]1[C:10]2[CH:9]=[N:8][C:7]3[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]=3[C:15]=2[N:14]2[N:16]=[C:17]([CH3:19])[CH:18]=[C:13]2[N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1358394108-ethyl-2-methyl-4-H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)-one

Product 1

HCID 537035595-chloro-8-ethyl-2-methyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine

Procedure

161 g of 8-ethyl-2-methyl-4H-pyrazolo[1,5-a]pyrazolo-[4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)-one (0.06 mol) are heated with stirring in 1 liter of phosphorus oxychloride at 80° for 48 hours. The mixture is decomposed by pouring onto crushed ice. The 5-chloro-8-ethyl-2-methyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine is filtered off and recrystallized from butyl alcohol, yield 148 g (86%); m.p. 179°-180°.

Workup

  1. additionby pouring
  2. customonto crushed ice
  3. filtrationThe 5-chloro-8-ethyl-2-methyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine is filtered off
  4. customrecrystallized from butyl alcohol, yield 148 g (86%)

Sources & evidence

ORD record
ord-73e3b4dae72c434091d65f3cd064a3f5
Source dataset
uspto-grants-1980_11
Patent number
US04233300

Reaction notes

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