Benzene → 2-Methyl-N-(1-methylpropyl)-6-phenyl-2H-pyrazolo[3,4-b]-pyridin-4-amine

HRID 65990Notes

Reaction equation

HRID 65990 reaction equation
Cl[C:2]1[C:3]2[C:4](=[N:14][N:15]([CH3:17])[CH:16]=2)[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.C[NH:19][CH2:20][CH2:21][CH3:22].[CH:23]1C=CC=CC=1>CCOCC>[CH3:17][N:15]1[CH:16]=[C:3]2[C:4]([N:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:7]=[C:2]2[NH:19][CH:20]([CH3:23])[CH2:21][CH3:22])=[N:14]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 12315N-MethylpropylamineHCID 22756855HCID 22756855, compound

Product 1

HCID 227568612-Methyl-N-(1-methylpropyl)-6-phenyl-2H-pyrazolo[3,4-b]-pyridin-4-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

14.6 g. of 4-chloro-2-methyl-6-phenyl-2H-pyrazolo [3,4-b]pyridine (0.06 mol.) and a solution of 100 ml. of methylpropylamine in 150 ml. of benzene are heated at 220° in an autoclave for 20 hours. After cooling, the mixture is evaporated in vacuo, and to the residue 100 ml. of water and 100 ml. of chloroform are added. After agitation, the chloroform extract is separated and dried with Na2SO4. Evaporation yields an oily product which, after treatment with ether, becomes solid. 14.3 g. of 2-methyl-N-(1-methylpropyl)-6-phenyl-2H-pyrazolo[3,4-b]pyridin-4-amine, (m.p. 148°-151° ), are recrystallized from ethyl acetate giving a pure product of the melting point 156°-157°.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is evaporated in vacuo
  3. additionof chloroform are added
  4. extractionAfter agitation, the chloroform extract
  5. customis separated
  6. dry with materialdried with Na2SO4
  7. customEvaporation
  8. customyields an oily product which
  9. customof 2-methyl-N-(1-methylpropyl)-6-phenyl-2H-pyrazolo[3,4-b]pyridin-4-amine, (m.p. 148°-151° ), are recrystallized from ethyl acetate giving a pure product of the melting point 156°-157°

Sources & evidence

ORD record
ord-22d25771c50e412ea5e7d2f071eb77f4
Source dataset
uspto-grants-1978_12
Patent number
US04129738

Reaction notes

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