3-(Trifluoromethyl)aniline → 8-ethyl-2-methyl-N-[3-(trifluoromethyl)-phenyl]-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]-pyrimidin-5-amine

HRID 1395222Notes

Reaction equation

HRID 1395222 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[N:9][C:10]3[N:14]([CH2:15][CH3:16])[N:13]=[CH:12][C:11]=3[C:6]=2[N:5]2[N:17]=[C:18]([CH3:20])[CH:19]=[C:4]2[N:3]=1.C(N(CC)CC)C.[F:28][C:29]([F:38])([F:37])[C:30]1[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH2:33]>C(O)CCC>[CH2:15]([N:14]1[C:10]2[N:9]=[CH:8][C:7]3[C:2]([NH:33][C:32]4[CH:34]=[CH:35][CH:36]=[C:30]([C:29]([F:28])([F:37])[F:38])[CH:31]=4)=[N:3][C:4]4[N:5]([N:17]=[C:18]([CH3:20])[CH:19]=4)[C:6]=3[C:11]=2[CH:12]=[N:13]1)[CH3:16]

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 537035595-chloro-8-ethyl-2-methyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine

Product 1

HCID 233316038-ethyl-2-methyl-N-[3-(trifluoromethyl)-phenyl]-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]-pyrimidin-5-amineYield 72.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5.8 g of 5-chloro-8-ethyl-2-methyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine (0.02 mol), 3 g of triethylamine and 3.3 g of 3-trifluoromethylaniline are refluxed in butyl alcohol for 24 hours with stirring. The solvent is removed in vacuo and the residue treated with 20 ml of water and filtered off. Recrystallization from alcohol yields 6 g of 8-ethyl-2-methyl-N-[3-(trifluoromethyl)phenyl]-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidin-5-amine; yield (73%) m.p. 205°-206°.

Workup

  1. customThe solvent is removed in vacuo
  2. additionthe residue treated with 20 ml of water
  3. filtrationfiltered off
  4. customRecrystallization from alcohol

Sources & evidence

ORD record
ord-d441c523c4634a499cd7ee1ce41fd21d
Source dataset
uspto-grants-1980_05
Patent number
US04202899

Reaction notes

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